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Holiday Rentals and Homes in Rockport, MA

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    Travellers to Rockport are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    5 of 5 stars (4) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    4.5 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2016!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 21 September 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and we...
    5 of 5 stars Reviewed 10 May 2015
    We come every year! It's a wonderful homey place- attractive, clean and convenient to everything. We don't even need a car when we come. This year we used the top floor guest...
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    1 / 10
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Mary's By The Sea offers a 1 bedroom ocean view apartment just sixty feet to the sand at Rockport's beautiful Front Beach. Only one block from downtown, our location is nicely situated for short walks to all the attractions Rockport offers. This clean and modern apartment is available for short or... View all property information
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    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 23 October 2015
    It was my pleasure and privilege to be a guest at Mary's by the Sea. The owners created a beautiful place for travelers to feel right at home. Everything you need to feel...
    5 of 5 stars Reviewed 1 September 2015
    Pat and Mary were very friendly and helpful hosts, right from the reservation and throughout our stay. We stayed in the ocean view apartment, which offered views of Front Beach...
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    1 / 7
    4.5 of 5 stars (8) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Inquire Winter Rates Specials Just as sweet as icing on a cupcake - This downtowner located in a court yard makes a perfect getaway since you can stroll to the beach and to all the cultural and seafood eateries located within a stones throw of your front door. The CORNERed INn is designed... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 17 August 2015
    I booked this property based on a few reviews form other vacationers. The location and cottage itself truly exceeded our expectations. The owner, Judy, was wonderful and so very...
    5 of 5 stars Reviewed 15 June 2015
    A little gem located a short walk to the beach, shops and restaurants that make up the lovely town of Rockport. I stayed with my adult daughter and we had plenty of space. We...
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    1 / 18
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
    • Outdoor Dining Area
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    • Porch
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    About this property
    Unique round house in quiet private courtyard just behind 40 main St. just steps to Front Beach. The outstanding feature is the rooftop deck with wonderful ocean views and breezes. Have your dinner up there and stay for the majical evening sunsets and stars. Galleries, restaurants, shops,... View all property information
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    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 23 August 2015
    The round house is PERFECT if you are a single or couple looking to enjoy Rockport. My wife and I spent a week in August here. We were lucky enough to have amazing weather for...
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    1 / 15
    4.5 of 5 stars (16) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Great location in seaside town. Walk to Bear Skin Neck shopping, art galleries and restaurants and the just opened Shalin Liu Performance Center in the heart of Rockport. Walk to Old Garden Beach. Rockport Train Station is located within a 5 minute drive drive. It is one hour train ride to Boston... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 21 September 2015
    Thank you Meg for 5 wonderful days in Rockport! The cottage is cozy, quiet, comfortable and felt very private as it is in a gorgeous and residential neighborhood very close to the...
    5 of 5 stars Reviewed 7 November 2014
    My husband and I spent 3 nights at the Carriage House and would love to return for a week. Great apartment, lovely decorations, very friendly host. Just a short stroll to harbor...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located on the ground floor of an antique sea captain's house,it is perfectly situated steps from Front Beach in the heart of the village of Rockport. Walk to the shops, restaurants, and world class performance center- The Shalin Liu. Enjoy sailing, kayaking, walking trails and much more. Relax in... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home.... View all property information
    Location Information
    Rockport, Cape Ann 01966
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Walk to Old Garden Beach in two minutes, Front Beach in 15 minutes and the shops and restaurants of Rockport in 12 minutes from our newly renovated one bedroom carriage house apartment. You will stay in a beautiful, quiet neighborhood where locals live throughout the year. The unit is in a separate... View all property information
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    Rockport, Cape Ann 01966
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    About this property
    Are you looking for an affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean and comfortable, for one or... View all property information
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    Rockport, Cape Ann 01966
    1 / 24
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    About this property
    The Mariner is a custom-furnished, luxury apartment with a panoramic harbor view and providing all the amenities and comfort that one may need to enjoy time in Rockport, Massachusetts. The Mariner, a 2nd floor apartment, is located at 35 Bearskin Neck. The front entrance is on Bearskin Neck and... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 4 weeks ago
    I grew up in Rockport and went home to visit family and friends. Could have stayed with family, however, checked on what was available in town. This newly renovated furnished...
    5 of 5 stars Reviewed 28 September 2015
    We loved the location and the apartment. It is right in the heart of Bearskin Neck in Rockport...easy walking to shops, restaurants and spectacular views. The apartment is very...
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    1 / 14
    5 of 5 stars (9) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 22 October 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    5 of 5 stars Reviewed 3 August 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
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    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Internet Access
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    About this property
    Built in 1900, this classic New England beach house is located in the Headlands neighborhood in Rockport, Massachusetts. Steps away is the charming Old Garden Beach, secluded enough to remain a hidden jewel of Rockport. Also a short walk away is the Headlands, providing spectacular views of... View all property information
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    Rockport, Cape Ann 01966
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
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    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach – Cape Ann Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of... View all property information
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    Rockport, Cape Ann 01966
    1 / 34
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This sweet and comfortable four bedroom, 1.5 bath cottage is just across the street from one of the most striking coves on Cape Ann - or anywhere for that matter - Folly Cove. Enter the cottage through the back door by walking through the large and verdant lawn with picnic table, into a small... View all property information
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    Rockport, Cape Ann 01966
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    This utterly sweet vacation rental cottage overlooking Rockport's beautiful Folly Cove has all modern amenities but maintains the ambiance of the year 1805, when it was built. A thoughtful eye has preserved the property's historical integrity while adding modern comforts. Bright and sunny, the... View all property information
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    Rockport, Cape Ann 01966
    1 / 26
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Mary's by the Sea in Rockport is located less than one block from downtown and directly across the street from Rockport's best attraction, Front Beach. Walk to shopping, restaurants and the many art galleries that old Rockport is known for. Enjoy excellent privacy from our spacious Ocean View... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 2 October 2015
    The description of this apartment was spot on. The corner kitchenette was actually an expanded hallway but it had a refrigerator, microwave, 2 different coffee makers...
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    1 / 8
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Perched over the Atlantic with spectacular views of ocean meeting sky. At the end of a cul de sac, this peaceful and quiet home on a private cove is only an hour north of Boston in a charming and historic beach town. Four bedrooms, three baths, newly renovated, two decks and sprawling lawn with... View all property information
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    Rockport, Cape Ann 01966
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    1 / 40
    5 of 5 stars (23) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    About this property
    PERIWINKLE COTTAGE - truly a place to call 'a home away from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's modern amenities. We have 2 units on one site. You are not able to reserve your stay through this site. For secure on-line booking... View all property information
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    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 27 June 2015
    My wife & I spent a week here from June 17th to June 24th 2015. We were very, very pleased with everything that was here at Periwinkle # 2. Everything that was shown and described...
    5 of 5 stars Reviewed 13 October 2014
    Form: The artwork, architecture and landscaping were aesthetically pleasing. Function: The rental was conveniently... centrally located, felt comfortable and safe, and had quality...
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    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Ocean Views
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    About this property
    Designed in classic cottage decor, our colorful and stylish cottage rental offers three bedrooms,with a king, a queen, and twin beds respectively, and two full baths (one with spa tub).. A large great room features comfy living space and a dining table and chairs. A full kitchen provides a... View all property information
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    Rockport, Cape Ann 01966
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This wonderful Rockport house, formerly an artist's studio, has been completely renovated into a luxury vacation home with harbor views. High ceilings, individually controlled high-end air conditioning units in each spacious room, and ample off-street parking are just some distinguishing features... View all property information
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    Rockport, Cape Ann 01966
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    From its waterfront perch this 4 bed/2.5 bath 3 level home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of the working cove, Sandy Bay, and the twinkling lights of the village of Rockport in the distance. The location of the home is ideal, away from... View all property information
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    Rockport, Cape Ann 01966
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    About this property
    Walk to Old Garden beach from this immaculate 4 bedroom home that was built in 2008, complete with its own HOT TUB. Just 0.7 Miles from the village of Rockport (and Old Garden Beach) with all its restaurants, galleries and shops, this is the perfect launching pad for your Rockport summer adventure.... View all property information
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    Rockport, Cape Ann 01966
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 and brought up to the highest modern standard, it retains its old world charm. It has wonderful architectural... View all property information
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    Rockport, Cape Ann 01966
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This wonderful 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 11 people, this is a house to bring the extended family to gather and... View all property information
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    Rockport, Cape Ann 01966
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Enjoy the best of all worlds in this spacious and bright, recently renovated vacation rental home that overlooks Rockport's stunningly picturesque Flat Ledge Quarry as well as vista views of Sandy Bay. If all this water makes you want to swim, you're in luck, because not only can you walk to the... View all property information
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    Rockport, Cape Ann 01966
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Rockport oceanfront! This sunny and immaculate vacation rental home couldn’t be closer to the water, situated on a bluff overlooking Sandy Bay and Pigeon Cove Harbor. Popples Cove House offers everything you could hope for in a vacation getaway – scenic views, location, privacy, comfort and air... View all property information
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    Rockport, Cape Ann 01966
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    A splendid 3 bedroom, 3 bath vacation rental home located in Rockport’s serene South End, Whale Cove Gardens provides each of its guests with a breathtaking and unforgettable experience. Surrounded by vibrant, award-winning gardens and jaw-dropping water views and located only 1.5 miles away from... View all property information
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    Rockport, Cape Ann 01966
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of 'The Avenues' at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this is a house to bring the... View all property information
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    Rockport, Cape Ann 01966
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Porch
    • Satellite TV
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    This delightfully summer vacation rental cottage, overlooking broad stretches of the Atlantic and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of what New England has to offer. Complete with two air conditioned bedrooms, an expansive yard, and a... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 42
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Grill
    • Patio
    • Porch
    • Air Conditioning
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    This waterfront vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor with unobstructed 180 degree views of the Atlantic, Sandy Bay, and the twinkling lights of the village of Rockport. The location of the home is ideal, away from all the hustle of town, but a 10 minute walk to... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 32
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Patio
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Enjoy ocean views of Rockport's famous twin lighthouses and walk to one of Rockport's best beaches in 6 minutes. This amazing 4+ bedroom vacation home allows you to sit anywhere on the main floor or deck and enjoy incredible ocean views of the Atlantic and Thatcher Island with its twinkling... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Internet Access
    • Porch
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    This gorgeous in-town Victorian vacation rental home offers the best of all worlds; it has been beautifully renovated, but it retains the old-world charm of 14 foot ceilings, huge windows and large rooms. Modern updates include all new baths, windows, refinished hardwood floors, walls and... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 38
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Walk to the beach, village and train to Boston from this stunning 4 bedroom/3.5 bath contemporary perched on a hill with cameo views of the twinkling village of Rockport and Sandy Bay. Exquisitely decorated and furnished to the highest standards, this home offers you a quiet and comfortable getaway... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 36
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    LONG BEACH. Step out the front door and into the sand and surf of this amazing beach. This 4 bedroom/2 bathroom cottage that sleeps up to 8, is a sunny and happy place, from the bright, large eat in kitchen, with a pass through to the formal dining area, to the radiant and open living area (with... View all property information
    Location Information
    Rockport, Cape Ann 01966
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
    other traveller has booked this property
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bearskin Neck and the village.... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Waterfront
    • Hot Tub
    • Patio
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    This immaculate beachfront 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 originating in Ireland via Nova Scotia to Cape Ann and back to France in 1884. Here is an excerpt from the May, 1884 'New... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This lovely 3 bedroom vacation home is appointed with high end appliances, finishes and furnishings while remaining very comfortable and accommodating inside and out. The house is located in the sought-after Marmion Way location which offers the ultimate Rockport experience: the convenience of a... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Midway between two picturesque destinations, the seaside village of Rockport, and the historic fishing port of Gloucester, Sage Hill is the perfect place for your vacation. Walk to Long Beach, as it is only .3 miles (less than a 7-8 minute walk), or take a short drive to Good Harbor Beach. Beach... View all property information
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    Rockport, Cape Ann 01966
    1 / 32
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Balcony
    • Internet Access
    • Satellite TV
    • Terrace
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Caleb's Beach House, a 3 bedroom/3 bath vacation home is a 3 minute walk to Old Garden Beach and only 3/10 of a mile to the picturesque village of Rockport with it's shops, restaurants and concert hall. Enter into the open floor plan living room (with fireplace), dining room and kitchen, which... View all property information
    Location Information
    Rockport, Cape Ann 01966
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Grill
    • Porch
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Parking
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Rockport, MA. Three hundred yards from the ocean, this charming home is located on lovely Cape Ann on the North Shore of Massachusetts. There is a small, secluded beach with a panoramic view of the coastline that can be reached by following a short country lane that passes by a salt water farm.... View all property information
    Location Information
    Rockport, Cape Ann 01760