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Cape Ann House Rentals

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    Travellers to Cape Ann are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    91 Matching Rentals in Cape AnnView all 141 rentals
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    Back Beach1 / 15
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming vacation rental home is situated just 300 yards from Whale Cove. Walk just 1 mile to a sandy beach or into the village of Rockport with its shops, restaurants, galleries and a world class Performance Center. Choose to cook your lobsters in the large, updated eat-in kitchen, which is...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This inviting family vacation home has bountiful space and is located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 6 bedrooms, 3.5 baths and the ability to comfortably sleep 10 people, this is a house for the extended family to enjoy. This area of Rockport...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    This aptly named home defined as an arrival at land on a sea or air journey offers a welcome respite for the visitor. Tucked away on a quiet side street in the picturesque Village of Rockport, Landfall offers privacy and calm, yet it’s just a short walk to Old Garden Beach and only 3/10 of a mile...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to France. Here is an excerpt...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Completely renovated 4 bedroom, 2 bath. Extraordinary home build in 1917. Incredible workmanship. Spacious designer kitchen w/ stainless steel appliances. Large Living room, Dining Room, and fours bedrooms (second floor). Central A/C! Close to town center, commuter rail, and Singing Beach. 4...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Beachcomber Suite1 / 11
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2017
    Fabulous food was awesome, she even irons the sheets! Highly recommend staying here. The breakfast was delicious.
    Reviewed 19 July 2016
    It was wonderful to be with Stephanie and Jay - their home is beautiful and welcoming. Stephanie's breakfast is not to be missed! I especially enjoyed the outdoor spaces - the...
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    About this property
    Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes daily multi-course gourmet...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large windows throughout, and with 4...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront historic vacation home is centrally located in the village of Rockport and was home to John Oakes in the late 18th and early 19th centuries. Completely renovated in 2015, it retains its old world charm. It has wonderful architectural details like an oversized (ornamental) fireplace,...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed 7 July 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and living...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Back Beach Cottages - Charming house & guest house1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2017
    There are two cottages located on the same property. The ocean views are amazing and downtown Rockport is just a short walk away.
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    About this property
    Back Beach Cottages are a unique 2 cottage property with stunning views of the ocean. The location offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The homes are steps away from Back Beach, a 5 minute walk to Front Beach and...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed 5 October 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
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    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A Year-Round Vacation Home1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    5 adultsHouse is in a great location.Very uncomfortable beds unfortunately. (In all rooms!) -wished there was a queen bed instead of a double in ocean view room-) there...
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    About this property
    $1750 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining room, and a masonry fireplace in...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Granite Pier is a traditional Cape Ann home with an unusual history. Built in the mid to late 1800’s, it was part of the Rockport Granite Company housing workmen who mined the nearby quarries. Blending traditional craftsmanship with modern amenities, this home is quintessential New England with...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large bay window and entertainment...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living room with plenty...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    Smoking allowed
    About this property
    This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful house your home base for your beach escape this summer. The main level of the home consists of the gracious and architecturally stunning sun...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
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    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located right around the corner from Gloucester’s fabled Stacy Boulevard, this completely renovated vacation rental home provides convenient access to downtown Gloucester. Gloucester Harbor and Stage Fort Park, with its beaches and playgrounds, are just a short stroll away and Main Street's shops,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dragonfly1 / 7
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed 30 August 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    About this property
    Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwasher, washer, dryer. Three...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and practicality. For comfort, each of the...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious and fully air conditioned vacation home boasts a lovely landscaped in-ground pool in a private, fenced-in yard. In the center of charming Rockport, the home is only two blocks from Old Garden Beach and Rockport harbor. A short stroll takes you to Bearskin Neck and its shops,...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Rockporter is a charming waterfront vacation rental home that sits on a quiet lane in Rockport's Pigeon Cove. You'll be as close to the ocean as one can be on Cape Ann, enjoying sweeping views of Sandy Bay from most rooms in the house. Set up to comfortably sleep 7, the house has an eat-in...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sandbars. Walk from this...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Captain's Cottage: Traditional setting with a private footbridge to the beach1 / 16
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2016
    We stayed here for a week and Loved it!! It's soo private and quite the only thing we could hear at night were the crickets and crashing waves of the Atlantic! The Captain's...
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    About this property
    This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape Hedge Beach. Just cross the lane and walk over the footbridge and you're on the beach! This cozy two bedroom beach house is pine-paneled, in the traditional summer cottage...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockport Hideaway: Private pool & a short walk to all Rockport has to offer.1 / 21
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We stayed here for a week in July. This is a really great house with all amenities. It is in a quiet neighborhood in Rockport yet only 5 mins walk from the shore and busy town...
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    About this property
    Spend your days at the beach or relaxing poolside by your very own private pool. Rockport Hideaway is also only a short distance from Rockport's shopping, dining and family activities. Leave the car and stroll to the village, beaches, schools (with tennis courts and playground), and the commuter...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My ocean view house with beautiful vistas was built by the Rockport Granite Company in 1817. It is a comfortable and bright 3 story house that can sleep 8, it has 4 bedrooms, 2 bathrooms, and 3 decks. The house in the scenic New England coastal town of Rockport, MA. P.S. The interior of the house...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Waterfront
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Straitsmouth Cove is a classic seaside 'cottage' in a sublime location on Rockport’s Gap Cove. This elegant vacation home has the rambling, comfortable feel of a vintage country manor by the sea. The expansive green lawn, with its incredible waterfront view, is a most serene and awe-inspiring...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Private Garden
    • Grill
    • Waterfront
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Last week of Aug. and all of Sept still AVAILABLE. Unobstructed OCEAN VIEW from every window! 3 BR HOUSE WEEKLY VACATION RENTALS - The Glenellen Cottage Delightful, late 1800's, newly renovated kitchen with 1st & 2nd floor full bathrooms, non obstructed Ocean View House on a rise overlooking...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This elegant and contemporary vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and north up the coast, the inside of the home...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis courts, newly...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Waterfront
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet comfortable living space....
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanside at Good Harbor is a waterfront vacation home directly on Good Harbor Beach, Gloucester's finest stretch of sand. Gracious and beloved, this family-friendly five bedroom summer cottage is set on picturesque Brier Neck. Sit on the waterfront terrace/patio and enjoy the summer breezes and...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated home. New to the 2014 season. Great for families. Rent just one town-home or rent the entire town-home w/ friends or family. This listing is for the first floor. Each residence has three bedrooms (two large bedrooms and bedroom/office). Office can be used as a third bedroom....
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a beach house, this is it. Walk to Long or Cape Hedge beaches in 5 minutes or just relax at this fun vacation rental home and enjoy the water views from one of two decks. Sea Vagabond House is actually two houses in one; the original cottage downstairs (which was built in...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pines is situated on over an...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two full bath home that boasts a...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Booth Cottage Ocean view, private path to beach. Private mowed path, ten minute walk to village, harbor, 2 parks, on the commuter rail, four bedrooms, three full and one 1/2 bath, extra large lawn for ball playing, large porches, high ceilings, large windows. 3000$ per week, lower rates off...
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    Location Information
    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Terrace
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch spectacular sunsets over the Essex River from the expansive deck of this one-of-a-kind vacation home. Clamshell Landing sits on 22 acres of pristine conservation land and overlooks the green grasses of the Essex salt marsh. Swim or kayak to the beach or out to lunch in Essex by way of the...
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    Location Information
    Essex, Cape Ann 01929
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Grill
    • Waterfront
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Good Harbor Beach views from almost every room --3 bedroom/3 bath home stylishly furnished with your beach vacation needs in mind. Just a 7 minute walk to Good Harbor Beach and lot's of space to play inside and out. Spacious rooms with hardwood floors, big kitchen to gather over meals, family room...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.1 / 17
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2016
    everything about this place was A+ ,the owners ,the apartment ,the location,the scenery,everything was awesome
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    About this property
    Welcome, cher ami ('dear friend'), to this gleaming second-floor vacation rental. Cher Ami is available as a summer rental and an off-season rental. Cher Ami is a spacious and sunny apartment, with 2 bedrooms plus an office space, an eat-in kitchen with an island, 2 bedrooms plus an office...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern one bedroom apartment with a new kitchen and updated bathroom, inside our contemporary home above Good Harbor beach. Privately separated with the front door as the main entrance. Open concept kitchen+ living room with dining seating for 6! Cool place to rest after a long day at the...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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