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Cape Ann Cheap Vacation Rental Deals

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    Travellers to Cape Ann are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    36 Matching Rentals in Cape AnnView all 147 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in Gloucester, MA, this home is a short walk...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let the stress melt away in the tranquil Atlantic breeze when you book your well-deserved getaway to this family-friendly Gloucester cottage. With soothing ocean views, access to a pristine private beach, and a peaceful location in a quiet neighborhood, you may never want to leave! This home lies...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    • Cable/satellite TV
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    Reviewed October 22, 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...
    Reviewed August 3, 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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    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...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Bright colors, rich fabrics, and antique furnishings make this three-bedroom home truly special. Enjoy a variety of amenities, including a full kitchen, a lush yard, and a patio with a gas grill, all three short blocks from the beach. Located on a quiet residential street, this Rockport home is...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Captain John Stephens House: Sparkling new studio in the heart of Gloucester1 / 24
    (1)Average
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Reviewed November 2, 2017
    When we walked into the rental, it was nicely decorated and very clean, but there were hidden problems. No air conditioning, and the damage deposit is nonrefundable. Had to...
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    About this property
    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 or couple...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Terrace
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    • Balcony
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    Pet friendly
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    Reviewed October 14, 2017
    Loved our stay at Gloucester Harborview Inn . Great location, spotlessly clean and very welcoming . Highly recommend
    Reviewed March 15, 2017
    I had a wonderful stay at this lovely charming bed and breakfast. Location, accommodations and hostess were excellent.Highly recommend!
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    About this property
    Are you looking for a conveniently located 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...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky shores and seafood markets. Dive...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Trade the stress of daily life for a laid-back retreat on the New England coast when you stay at this charming Rockport vacation rental. Up to 12 guests will enjoy home comforts such as a private washer/dryer and free WiFi, not to mention a beautifully styled interior and a spacious deck with ocean...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    My place is close to walk to or short drive to restaurants and dining, family-friendly activities, the beach, nightlife, whale watching . You’ll love my place because of the coziness , the comfy bed, the relaxed and easy atmosphere, and close proximity to all Gloucester, Rockport and Cape Ann have...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Ocean Views
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience old charm like never before in the idyllic North Eastern town of Rockport at this cozy vacation rental apartment. Shiplap walls, wide planked floors, and original exposed beams make this 1-bedroom, 1-bathroom home the perfect romantic getaway for 2. Walk out your front door and find...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sea Mist Cottage1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Reviewed November 11, 2017
    We came to celebrate our 32nd anniversary. We absolutely loved the Seamist cottage. There were did many wonderful details that were put into this place, we couldn't list them...
    Reviewed August 14, 2017
    We were extremely happy with our stay. The cottage was very clean and had an ocean theme through out. Everything we needed was there! Our daughter (14) slept in the loft and...
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    About this property
    Seamist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. Short walks to shopping and art galleries on Bearskin Neck, beaches, train station as well as the Shalin Liu Perfomance Center. We, as new owners, welcome inquiries & feedback....
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    Reviewed September 20, 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed January 27, 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...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The dining area and deck overlook a gardeners delight of perpetually blooming flowers surrounding a Koi pond a beautiful woodsy backdrop - the backyard is a slice of heaven, and yours to enjoy when you stay at Serenity. This home is nestled in a quiet neighborhood surrounded by attractions like...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    Mark's rental apartment in Gloucester is my all-time favorite rental home! It offers a comfortable queen-sized bed, an additional bedroom with a twin, a living room with a small...
    Reviewed October 5, 2017
    When we arrived our host met us at the door and let us in, the first thing we noticed was the wonderful view and a balcony to sit on. We were close to most places by walking.
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    About this property
    Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING1 / 12
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Balcony
    • Outdoor Dining Area
    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2018
    What a wonderful place!! I had the upstairs to myself as well as a living room. Wendy has thought of everything! Very hospitable. I wish I could have stayed here for a month...
    Reviewed March 6, 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
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    About this property
    WEEKLY BOOKINGS ACCEPTED NOW FOR SUMMER 2019!!. 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, WIFI, cable TV and microwave kitchenette, private entrance, private bathroom all on...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet1 / 23
    (35)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 3 weeks ago
    The perfect cottage located on a quiet street that's walking distance to everything. Anything we thought we should've brought but didn't was already there provided by the owner...
    Reviewed September 25, 2018
    Great place and location. I would recommend the place to anyone. The extra touches are to numerous to mention but here are few: chocolate kisses, cream for coffee, bottle of...
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    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2018... we're honored to celebrate our 9th year hosting guests from all over the world! 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...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come together with your friends and family for the trip of a lifetime at this Gloucester vacation rental cottage for 12! Three bedrooms, 1.5 bathrooms, plus a detached log cabin, create the perfect retreat - where you'll be ruled by the ocean's high and low tides and unforgettable sunrises and...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Close to Half Moon Bay1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Modern comfort meets colonial charm at this gorgeous home on the banks of Lobster Cove. Beautifully designed, with a gourmet kitchen and abundant skylights and windows that gaze out onto tranquil views of the water, this updated house offers coziness and elegance in equal measure. A quiet...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    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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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and restaurants.The new...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 25
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed November 24, 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
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    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Private Garden
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Bed & Breakfast is located in the small New England coastal town of Essex, MA. on Cape Ann. Historic farmhouse built in 1695 on 18 pristine areas of forest, fields and meadows. First free school in state. Front field used during Revolutionary War for militia training. House completely updated...
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    Location Information
    Essex, Cape Ann 01929
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed June 27, 2016
    We really enjoyed our stay. Originally from Massachusetts, we looked for a place that would be interesting and relaxing. The rental is perfect. We were comfortable, had...
    Reviewed February 19, 2016
    With two bedrooms, a convenient, well-stocked kitchen, and a homey living room, the Salty Dog was just what we needed for a family getaway to Rockport, MA. Owners were friendly...
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    About this property
    The Salty Dog Summer Stay is a spacious, bright, furnished apartment with all the comfort and amenities one may need to enjoy time in our seaside town. Perfectly located on Atlantic Avenue in the Old Garden Beach neighborhood, many of Rockport's shops, restaurants, and attractions are a short walk...
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    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the deck of this New England vacation rental home are picturesque views of Rockport Harbor and iconic Motif #1, the area's prized historical landmark. Minutes from delightful shops and restaurants in Rockport, this conveniently located 1-bedroom, 1-bath second-story condo is only 20 minutes...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rockport in town private cottage within walking distance to town and all Rockport has to offer: beaches, restaurants, art galleries, shops, Shalin Liu performing arts center, Bearskin neck and the train. *The cottage is 2 floors. On the first floor is a fully equipped kitchen, with a cooler for...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Captain Quarters1 / 14
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Changing Tides is true it's name. I arrived stressed and tired from my daily grind but, left relaxed, rested and full of wonderful memories! Stephanie and Jay are more than...
    Reviewed July 8, 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
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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....
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    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 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 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    • Private Garden
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A large, bright and cheery front bedroom with two Queen size beds – private bath with clawfoot tub and shower. Newly constructed bathroom with vintage fixtures and repurposed woods. Our breakfast room has old pine cupboards, creeping ivy with twinkling lights, lace tablecloths and original vintage...
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    Location Information
    Essex, Cape Ann 01929
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 19th century apartment has the look of feel of the original cottage that it once was. This property is located on a side street in Essex that ends in the adjacent pristine woods. Connected to the quiet owner's home, this 'cottage' has it's own entrance, driveway and integrity and is...
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    Location Information
    Essex, Cape Ann 01929
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester with easy access to highway....
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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