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Holiday Rentals nearby Wingaersheek Beach

Gloucester, Massachusetts
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    Travellers to Gloucester are booking May dates now. Secure your holiday home today, and have the perfect trip.
    All 64 Rentals in Gloucester
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 30
    (17)Excellent
    5.6 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Stunning SUNSET STUDIO w/Scenic Harbor View1 / 29
    (5)Excellent
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4.8 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5.9 kilometres from Wingaersheek Beach
    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Golden Sands is the quintessential turn of the century Gloucester beach 'cottage.' With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach house. The main level includes...
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    Gloucester, Cape Ann
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 12
    5.5 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Glamorous Gloucester Getaway 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...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lovely 'Blue Heron Cottage' on Annisquam River!1 / 24
    (1)Excellent
    4.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
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    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
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    About this property
    Enjoy a peaceful retreat in coastal New England by staying at 'Blue Heron Cottage' - a lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    La Boheme RETREAT Studio1 / 26
    (3)Very good
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Waterfront
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    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 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 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...
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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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    5.8 kilometres from Wingaersheek Beach
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed 26 October 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
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    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage...
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
    5.9 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.7 kilometres from Wingaersheek Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Waterfront
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pines is situated on over an...
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    1.7 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurston Point Cottage offers a relaxing atmosphere with spectacular sunset views over the Annisquam River. You might choose to sip a cool drink on one of the large porches and watch...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    5.9 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fabled boulevard and the “Greasy...
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    2.3 kilometres from Wingaersheek Beach
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed 7 July 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    5.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home (formerly known as Strawberry Cove House) with spectacular views and top-notch amenities. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, water views abound from almost every light-filled room. The house...
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1.3 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo. This home has a custom kitchen, spacious open concept living/dining room and...
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.9 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Good Harbor Haven Good Harbor Haven is a charming home that would be perfect for your next beach getaway. The home has a lovely interior with room enough for the whole family. It also has complimentary WiFi and cable for your enjoyment. Be sure to take advantage of the lovely yard with gas grill...
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    5.6 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Located in a quiet, leafy neighborhood, Family Tides offers convenience and comfort, just a half-mile to Gloucester's Good Harbor Beach. Cathedral ceilings with skylights, large picture windows, and French doors to the deck illuminate the the open-plan main floor. Starting in the fully-applianced...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.8 kilometres from Wingaersheek Beach
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    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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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bathroom, Sleeps 2
    4.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picture yourself on the huge wraparound deck of Ships Bell House, enjoying the setting of the sun over breathtaking water views. That's the moment you'll never forget when you stay in this charming vacation rental home in Gloucester's Lanesville neighborhood. Ships Bell House is located on a...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.2 kilometres from Wingaersheek Beach
    6 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    About this property
    Cedar Ledge Annisquam (formerly known as Annisquam Heights) is a classic New England vacation home that pays homage to the past but has modern sensibilities. From the vast wraparound porch, you'll be able to relax and catch salty sea breezes while taking in the incredible ocean views. Inside, the...
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 14
    1.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect vacation spot. The bright and airy ground floor has many windows, letting in lots of natural light. Upstairs, there are 3 bedrooms and a full bath with claw foot tub and...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    5.8 kilometres from Wingaersheek Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Property for 2020. Plaisance is a comfortable modern home nestled in a quiet, leafy neighborhood not far from Good Harbor Beach and the Bass Rocks Golf Club. The ground floor is open and airy and lets in plenty of natural light throughout the day. The living room is perfect for keeping the...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spectacular vacation rental home is situated in the heart of Annisquam, overlooking picturesque Lobster Cove. You'll enjoy water views from every window, choose from multiple patios for relaxing, and so much more! Lobster Cove House boasts high-end furnishings and appliances, a landscaped...
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    5.6 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home base for your Gloucester beach vacation with family or friends. Over By Good Harbor sits prominently on a grassy knoll with abundant views of Good Harbor Beach and the sea beyond....
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of the Ipswich Bay from the upper level. Decorated with a European sensibility, the home is sunny, comfortable and cheerful, with hardwood floors throughout. A Queen Anne-style house, you can access the...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    5.6 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Enjoy the charms of Rocky Neck from this light-filled vacation home with hand painted antique ceilings and water views from almost every window. Your inner chef will love the beautiful cook's kitchen with stainless commercial grade appliances, including a 6-burner gas stove, wine fridge, and...
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll find river life at its best when you stay at this newly-built vacation rental home that sits along the banks of scenic Annisquam River in Gloucester. From the private patio, you will be mesmerized by spectacular sunsets and the parade of boats as they sail, motor, or paddle by. Annisquam...
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    5.7 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 3, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    5.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Large outdoor shower close to beach, restaurants, fun This sparkling, fully updated 3 bedroom one level beach house sleeps 7, and provides a private getaway that is convenient to all. It is freshly painted and has new appliances and WiFi and a flat screen TV in living room, a large outdoor shower,...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    2.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Gloucester, America’s oldest seaport! This two acre, family-friendly, contemporary private retreat on Gloucester’s Rust Island offers 4 Bedrooms with stunning panoramic views of beautiful marshes and the Jones River, which flows into the Annisquam River and Ipswich Bay. Surrounded by...
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    6.0 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    • Ocean Views
    • Internet Access
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    4.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    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...
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Waterfront
    • Grill
    • Ocean Views
    • Patio
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    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront tri-level, with 4 bedrooms, 2 full baths, fire pit and a dock will accommodate up to 10 people. Located on Little River overlooking the water, the yard, screened porch and patio face west for the most spectacular sunsets. Launch your trailered boat at the public launch or use your...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    1.9 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Internet Access
    • Grill
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An excellent holiday starts with a great view at a unique place that suits your needs. This little boat house is right in front of the water. You'll hear the water and enjoy a few boats around. The sunsets over the water and across the other side are spectacular. Enjoy just a simple life: sitting...
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    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Greet each day with inspiring views of the Annisquam River from this charming vacation home and enjoy the most spectacular sunsets each evening. Terra Nova offers that 'get away from it all' feeling, with a large verdant lawn, breathtaking water views, and comfortable furnishings. Inside, find an...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Waterfront
    • Grill
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated home is located directly on Lobster Cove in the historic village of Annisquam. Around 1623, Captain John Smith described the cove as a 'a safe harbor in a Northeast storm.' Nothing has changed. Swim from your own private dock where there is a paddle board and kayak for...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.1 / 27
    (1)Excellent
    2.7 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I highly recommend this location. The house is wonderful, super cute, super clean, and has EVERYTHING you could possibly need (we especially appreciated the beach chairs...
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    About this property
    Cottage at the Cove is a bright, inviting vacation home situated in Gloucester's charming Bay View neighborhood that radiates an aura of sun and warmth. Just a short walk down the lane to Plum Cove Beach to spend your summer vacation relaxing by the water, discovering local fauna, swimming to your...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Cool Cove: Wingaersheek Beach plus your own private beach & all those views!1 / 21
    (1)Very good
    0.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2019
    The house had a sugar ant problem, toilets ran and circulation was bad. Also it says it has air conditioning but that is only 1 room. We had a family of four and had to time out...
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    About this property
    Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sandbars. Walk from this...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.8 kilometres from Wingaersheek Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and three full baths as well as a lovely eat-in kitchen, formal dining and living...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    The Sail Loft of Bearskin Neck- Old Harbor Retreat1 / 17
    (1)Excellent
    6.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
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    • Ocean Views
    • Patio
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    We loved our stay at the Sail Loft—the apartment has all the amenities we needed (including air conditioning!) and was a pleasure to cook and relax in. If you like being in the...
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    About this property
    The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV with Netflix and Amazon Prime TV & dining table that can fit up to 6. There is a small patio in front with a table, bench...
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    Location Information
    Rockport, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Back Beach1 / 15
    (2)Excellent
    5.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Garden
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
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    About this property
    Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mile down Granite Street for a...
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    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet1 / 23
    (44)Excellent
    5.5 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Cable/satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2019
    This is truly a home away from home. A short walk to town where parking is at a premium. Stocked with everything you might need, with extra touches like a new kitchen sponge...
    Reviewed 28 July 2019
    Dear Rosemarie and Family!Our second lovely stay in #1 Periwinkle Cottage!So rejuvenating – we had to stay the extra day! We are very grateful for the ease of keeping our...
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    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2019.. Celebrating our 10th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call 'a home from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's modern amenities. (You...
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    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    5.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vintage Rockport Escape Bright colors, rich fabrics, and antique furnishings make this three-bedroom, dog-friendly 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...
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    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.9 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
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    • Waterfront
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Rockporter is a charming waterfront vacation rental home that sits on a quiet lane in Rockport's Pigeon Cove. You'll be as close to the ocean as one can be on Cape Ann, enjoying sweeping views of Sandy Bay from most rooms in the house. Set up to comfortably sleep 7, the house has an eat-in...
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    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    5.5 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Cable/satellite TV
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or, walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier is spectacular, and even...
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    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    5.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2016
    We just completed our first visit here and plan to return to this house. A Very clean, historic home that more than met our expectations. It is off the beaten path with both...
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    About this property
    Down a quaint lane you will find an Artists cottage and guest suite. The smaller of the two buildings contains a private double bed retreat with en suite, cable TV & Wi fi. The Main house boasts a charming loft bedroom with 2 ex-long twin beds. The ceiling of the second floor bathroom is a large...
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    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy all that Cape Ann has to offer at Happy Days Cottage, across the street from enchanting Folly Cove. Right at the waterfront, there is a shared deck from which you can take in the views, or you can walk down to the water to swim or launch your kayak. The cottage is bright and...
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    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Quarry Crest House: Includes swimming rights to Little Parker quarry1 / 27
    (1)Excellent
    5.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2017
    We had a really nice vacation staying at Quarry Crest House in Rockport with our daughter, son-in-law and 23-month old grandson for nine days. The house was perfect for us with...
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    About this property
    Enjoy the best of all worlds in this spacious and bright vacation rental home overlooking Rockport's stunningly picturesque Flat Ledge Quarry. Not only can you walk to town or to the beach in a few minutes, but you can also swim at the nearby quarry, Little Parker's Pit. This is a sparkling fresh...
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    Location Information
    Rockport, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING1 / 12
    (7)Excellent
    5.6 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2020
    Wendy was a fabulous hostess! We had a kitchen stocked with cereals, milk, soda and cold water in the fridge, ice, and even a small cooler on top of the fridge. Wendy was warm...
    Reviewed 24 August 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...
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    About this property
    WEEKLY BOOKINGS ACCEPTED NOW FOR SUMMER 2020!!. 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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    Location Information
    Rockport, Cape Ann
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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