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Holiday Rentals and Homes in Ipswich, MA

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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 13
    5 of 5 stars (2) Excellent
    Ipswich
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ipswich
    5 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
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    About this property
    Nestled on Little Neck hill just a short walk to Pavilion beach and River Road beach across from Crane Beach, this home is cool and relaxing. Covered in giant old trees with distant views of Plum Island Sound and Ipswich River channel. Your get-away! This cottage is beautifully weather-worn and one... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Parking
    • Porch
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    One of the few seaside old family cottages of Gloucester that is ready to welcome you for a unique experience. Fully equipped with a gorgeous view of colorful sunsets and a home that delivers a great living space near Halibut Point on the water. A very large home with 4 bedrooms and bunk room;... View all property information
    Location Information
    Ipswich, Massachusetts 01930
    Ipswich
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Waterfront
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    • ?
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    • x
    About this property
    The most elegant room in the house with sitting area in front of a fireplace and private bath. Enjoy this charming New England B&B with scrumptious complimentary breakfast. Just a 5 minute walk to the sea river channel. 9.7% tax included. This home is one of the 59 First Period houses of Ipswich,... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    A colonial style B&B with full-on New England hospitality, style and farm-house breakfast. The room is comfortable with twin beds and a private bath. Lots of relaxing space. Near the channel river and downtown restaurants, not to mention Crane Beach. Room type: Private room Property type: Bed &... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Garden
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    A great experience in an old New England home renovated into a gracious bed & breakfast residence. Immediately be engrossed in the traditional feel of the old woodwork and flooring. An outside deck for warmer days and a fireplace sitting room for chilly evenings and winter days. The rooms include... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
    • Waterfront
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    • Washer
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    High-lights of Scandinavian design throughout the house will give a sense of tranquility as the breezes pass through a nice old-fashioned screen porch. Two large long tables for dining inside or out help to bring friends and family together. The kitchen, dining and porch space are the focus of this... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Garden
    • Outdoor Dining Area
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    The Carriage House bedroom has two queen beds, a large private bath, television, air conditioning, and telephone. There is a mini kitchen with the addition of a second sink, microwave, and refrigerator. This is a very comfortable large room with all of the amenities you would need to stay for more... View all property information
    Location Information
    Ipswich, Massachusetts 01938
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    Ipswich
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    The Swedish Room is themed with open wood plank floors and hand-crafted bed cover. It is particularly cozy with sun-streamed angled dormers and built in closet and drawers. It can accommodate up to 4 people with its queen and twin beds. Private bath. One of New England's most charming B&Bs with... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Shared Garden
    • Outdoor Dining Area
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    A charming New England B&B just a 5 minute walk to the sea river channel. Complimentary breakfast and wifi included. This room is spacious with a mini-kitchen including a microwave and Keurig coffee maker. Private bath. Price includes 9.7% tax. The home is charmingly antique and yet updated for... View all property information
    Location Information
    Ipswich, Massachusetts 01938
    Ipswich
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Shared Garden
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The quaint town of Ipswich, Massachusetts is one of the oldest settlements in the United States, originally inhabited by Native Americans and later colonized in 1633. Thanks to Ipswich’s close proximity to the Atlantic Ocean and Ipswich River, Ipswich continues to be one of the state’s top... View all property information
    Location Information
    Ipswich, Massachusetts 01938

    The following rentals are within 15 kilometers of Ipswich, Massachusetts.

    1 / 25
    5 of 5 stars (6) Excellent
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
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    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spacious 5 Bedroom Brick Colonial Home located on the Historic Stacey Boulevard with picturesque views of Gloucester's Harbor and the Atlantic Ocean. Look out at the stunning views of local schooners, the light houses, fishing vessels and feel the cool sea breeze that provides refreshment from the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 19 May 2016
    Our group was extremely pleased with our stay at Pratt House. We enjoyed the large and immaculate living room, dining room, deck and yard. The location across the street from...
    4 of 5 stars Reviewed 10 May 2016
    We are so fortunate that Marilyn shared here beautiful house with us for our annual girl get together. The spacious dinning room, living room and back deck afforded plenty of...
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    1 / 8
    4.5 of 5 stars (4) Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy all that Gloucester has to offer in this charming 1BD cottage by the harbor in East Gloucester. Located on East Main street, so busy during the day, quiet at night. Close to everything by foot or bicycle. $1,150 off season monthly rate from Nov to April. 30 day minimum off season. New gas... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 9 September 2015
    This place is so well-located, well-designed, comfortable and easy! It allowed us a much needed break with access to all the beauty of Gloucester. I loved rocky neck, biking to...
    5 of 5 stars Reviewed 5 August 2015
    This is the perfect cottage for a couple retreat. It is a home away from home. Conveniently located for walks and picture taking. We will defintely stay here again when we...
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    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Turn of the century home located two blocks from Atlantic shoreline and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat. Large modern fully equipped kitchen with double oven, 6 burner stove, dishwasher, washer, dryer. Three fireplaces,... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 43
    4 of 5 stars (1) Very good
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lovely cottage set high up on a hill overlooking the private section of Wingaersheek Beach, this lovingly restored 3 bedroom home has been in the same family for over 55 years. The cottage boasts one of the most spectacular hilltop views on the entire beach with meticulously maintained lawn and... View all property information
    Location Information
    Gloucester, Cape Ann 02116
    4 of 5 stars Reviewed 20 July 2015
    Great beach get away. Walk to private beach. Cottage was very cute and clean with nice deck, outdoor shower, and pretty gardens. Cottage was well equipped with linens, towels...
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    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back memories of long ago. At the end of a dirt road, the cottage offers a wrap around porch, rolling green grass, granite steps leading to a flat rocky... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 12
    5 of 5 stars (15) Excellent
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This tastefully decorated, immaculate one-bedroom vacation rental is on the first floor of a landmark Victorian, with private entrance off a grand wrap-around covered veranda, overlooking private fenced-in lawn and garden. The covered veranda provides a great cooling respite from the sun in summer... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 2 July 2013
    My family and I have stayed at Good Harbor house for the past five or six years. We have been coming to Gloucester every year for more than 20 years. Good Harbor house is, hands...
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    1 / 40
    5 of 5 stars (3) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Terrace
    • Waterfront
    • Wi-Fi
    • Balcony
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    All utilities are included. Heat, electricity, water, basic cable. Full hi-speed wifi Sq. footage 1200 sq ft. Full Bathroom with shower Walk in closet Parking: off street Pets Policy: no pets preferred but exceptions upon request Kitchen has a Range/oven and Refrigerator, toaster, coffeemaker,... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 1 week ago
    This apartment is totally off the beaten path -- in the back of the second floor of an ancient office building, and right on the commercial harbor. You walk up the stairs and...
    5 of 5 stars Reviewed 19 April 2016
    Every window offers a stellar view of the water. In fact, the balcony is actually over the water. This is the best location Glouscester could ever offer. It's a large, weirdly...
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    Beverly
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • Parking
    • Waterfront
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to the Harborfront House, located at historic Independence Park and Beach on Lothrop Street, recently recognized by the Boston Globe as one of the “20 Best Streets in Boston and Beyond'.<BR>You will be instantly captivated by the waterfront activity just steps from the front... View all property information
    Location Information
    Beverly, Massachusetts 01915
    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 22
    4 of 5 stars (4) Very good
    Gloucester
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    LAST MINUTE CANCELLATION allows summer RATE DISCOUNT on authentic English Manor Home reminiscent of the Cotswolds. 'Misselthwaite Manor' is a a quiet respite in a busy world, yet close to everything Historic Gloucester has to offer. Located in the heart of the private peninsula of Eastern... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    4 of 5 stars Reviewed 17 November 2014
    Beautiful home. Open beam construction. Impressive wooden entry door with iron work fixtures. Soothing relaxing music playing in the breakfast room. Walled in yard with gated...
    4 of 5 stars Reviewed 6 September 2014
    We found the house to be in good order. The kitchen had everything we needed to cook once in a while when we didn't dine out. The bathrooms and bedrooms were nice and clean. Lois...
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    1 / 12
    4.5 of 5 stars (2) Very good
    Gloucester
    6 Bedrooms, Sleeps 12 | Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    4 of 5 stars 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...
    5 of 5 stars 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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    Gloucester
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Waterfront
    • Satellite TV
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    • Ocean Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house just steps from the private end of Good Harbor Beach. Open and airy living space with spectacular views of the beach, modern kitchen with all the amenities, large dining area for... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 26
    5 of 5 stars (13) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Waterfront
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. <BR><BR>Open living space - large living room with sliding door onto large private deck overlooking... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 4 weeks ago
    We had such a great experience staying at Summerwind two years ago that we recently returned. With three teenage boys we found it extremely convenient to have boogie boards...
    5 of 5 stars Reviewed 20 June 2016
    Summerwind Cottage is an absolute jewel! We loved the beautiful, artistic decor, and our hosts, Linda and Hank are just the best. Linda's suggestions were all fantastic. We fell...
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    1 / 33
    Gloucester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Satellite TV
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Direct waterfront on picturesque Goose Cove, this immaculate 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... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 26
    5 of 5 stars (2) Excellent
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Washer
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    • Patio
    • Central Heating
    • Ocean Views
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    UNPLUG, UNWIND & UPLIFT YOUR SPIRITS! For those seeking to truly rest, relax and rejuvenate - we can't wait to meet you! Decorated in charming, boho style with creative objects d'art and romantic, atmospheric lighting. A petite solarium brings strong morning light. Beautifully designed outdoor... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
    5 of 5 stars Reviewed 25 January 2015
    We stayed here and had a delightful week in Gloucester ~ a cozy, romantic and uniquely decorated apartment ~ very aesthetic with extra ammenties ( ie, a washer & dryer) and a...
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    1 / 17
    3 of 5 stars (1) Average
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A delightful vacation home situated in Gloucester's charming Bay View neighborhood, Annie's Place radiates an aura of sun and warmth. Only an 8 minute walk to lovely Plum Cove Beach, Annie's Place lets you spend your summer vacation relaxing, discovering local fauna such as hermit crabs, and... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    3 of 5 stars Reviewed 29 July 2015
    Cute house with a terrible parking/road situation. Poorly maintained exterior and patio made walking around the TINY yard dangerous for kids and those with mobility/vision...
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    1 / 26
    Gloucester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Patio
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 24
    Beverly
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
    About this property
    Toast the glow of another gorgeous day on the riverfront wraparound deck of Afternoon Delight in historic Beverly. A decorative columned portico and farmer's porch welcome you into to this immaculate and restful vacation rental home. Start in the foyer which opens to a carpeted living room with... View all property information
    Location Information
    Beverly, Massachusetts 01915
    1 / 16
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Walk to Good Harbor in 7 minutes from this NEW one bedroom apartment. Completed in July of 2015, this vacation home is pristine and waiting just for you. Enter through your own entrance into the bright granite kitchen with an A/C unit, a table for 4, and stainless appliances. Pass through to the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 17
    5 of 5 stars (3) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 4 weeks ago
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
    5 of 5 stars Reviewed 3 May 2016
    Loved this place. Looks out over the water and was very comfortable. The owner was super, she made sure we had everything we needed and even left a binder full of places in the...
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    1 / 13
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This Friday to Friday vacation rental is right at Good Harbor Beach. Step out the door, walk over the Good Harbor Beach footbridge and you are on one of Gloucester’s most highly rated beaches enjoying the sun, sand, and surf. Leave your car in the driveway and enjoy the best of summer; run home for... View all property information
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    Gloucester, Cape Ann 01930
    1 / 27
    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Terrace
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacey 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,... View all property information
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    Gloucester, Cape Ann 01930
    1 / 19
    Gloucester
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Waterfront
    • DVD Player
    • Internet Access
    • Satellite TV
    • Patio
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the views of the sparkling waters of the Annisquam River and Ipswich Bay beyond as well as Wingarsheek Beach and the Annisqaum Yacht Club just across the river. Don't forget the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 25
    Essex
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
    • Porch
    • DVD Player
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This delightful vacation rental home offers gracious comfort and easy access to the riverfront town of Essex, with its multitude of antique shops and restaurants. Enter the home via the stately front porch complete with rocking chairs, making it the perfect shady perch to watch the world go by.... View all property information
    Location Information
    Essex, Cape Ann 01929
    1 / 54
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • Satellite TV
    • Porch
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. From the side entrance on a quiet lane, you will step into a bright back hall with... View all property information
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    Gloucester, Cape Ann 01930
    1 / 24
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the... View all property information
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    Gloucester, Cape Ann 01930
    1 / 18
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
    • Internet Access
    • DVD Player
    • Porch
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Situated on the shores of the tidal Mill River on a shaded lot of nearly one acre on Gloucester's Wheeler's Point, this vacation home has its own dock and float. This three bedroom, two bath house is on one level and features an open plan concept with cathedral ceiling and lovely water views. The... View all property information
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    Gloucester, Cape Ann 01930
    1 / 24
    Gloucester
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    About this property
    New in 2016! Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual... View all property information
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    Gloucester, Cape Ann 01930
    1 / 30
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    • Porch
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Taking its name from the glorious sunsets one has the privilege of viewing from each of its rooms and both of its decks, Sunset Cottage is a renovated 2 bedroom, 1 bath cottage in Gloucester’s Thurston Point district. Sunset Cottage sits directly on the tidal Annisquam River and boasts air... View all property information
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    Gloucester, Cape Ann 01930
    1 / 28
    Prides Crossing
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    On a gorgeous estate, this Beverly Farms Carriage house has been lovingly renovated and made into 3 tasteful and comfortable units. This air conditioned rental includes use of the estate swimming pool, tennis court, private beach, and hot tub. It is located just a half a mile from West Beach which... View all property information
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    Prides Crossing, Massachusetts 01915
    1 / 32
    Gloucester
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Grill
    • Porch
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Gloucester, Cape Ann 01930
    1 / 32
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • DVD Player
    • Porch
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New in 2016! Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines offers everything you could want in a vacation rental home, with five bedrooms, two full bathrooms and a tidal dock.The house is situated on over an acre of... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    other travellers have booked this property
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    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Gloucester, Cape Ann 01930
    1 / 28
    Newburyport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Porch
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    SEPTEMBER 2015 UPDATE: We have rented this property with a long term tenant at the moment. - Thank you for your interest. Perfect for a professional on assignment, a visiting couple who want to to be a walkable distance from downtown Newburyport, anyone in housing transition. Description... View all property information
    Location Information
    Newburyport, Massachusetts 01950
    1 / 29
    5 of 5 stars (10) Excellent
    Gloucester
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Patio
    • Grill
    • Internet Access
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This oceanfront year round home was recently constructed to maximize spectacular ocean views and sunsets. Enjoy the views of the water outside while sitting on the glassed in balcony just off of the master bedrooms , the screen/glass windows across the front or on the stone patio or dock. Inside,... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 2 October 2012
    We were two families (four adults, 3 children and a toddler), and everyone had a wonderful time. Wingarsheek and Crane Beaches are reasonably convenient, as are some great...
    5 of 5 stars Reviewed 1 May 2012
    We were eight women celebrating over 50 years of friendship with a long weekend getaway. We were delighted with The Landry Cottage. The spacious house is brightly and...
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    1 / 21
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Captain's Watch House is a Gloucester vacation rental located just a lane away from iconic Stacey Boulevard. This 3 bedroom/1.5 bath gem is steps away from the harbor, two beaches, glorious Stage Fort Park and the vibrant downtown with a huge array of restaurants, galleries, shops, museums and... View all property information
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    Gloucester, Cape Ann 01930
    1 / 6
    4 of 5 stars (1) Very good
    Gloucester
    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Updated seasonal waterfront cottage ideal for swimming or kayaking right from the property. It is located on the Northeast shore of Cape Ann, affording sweeping views of Ipswich Bay, with gorgeous summer sunsets over the water. It is nestled in among three other waterfornt cottages in a quiet... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    4 of 5 stars Reviewed 27 September 2015
    We stayed at this glouster harbor house for a wedding weekend. Ten of us stayed comfortably. The house is furnished with everything you need. Dr. Rick was wonderful with prior...
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