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Holiday Rentals near Wingaersheek Beach

Gloucester, Massachusetts
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    Travellers to Gloucester are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 114 Rentals in Gloucester
    1.7 kilometres from Wingaersheek Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    1.7 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    5.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
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    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
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    Pet friendly
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    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
    2.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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
    4.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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 6 Quick View
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    • Waterfront
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    About this property
    Waterfront tri-level, with 3 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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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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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
    4.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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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    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
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    Smoking allowed
    About this property
    Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the second floor bedroom with deck. Decorated with a European sensibility, the home is sunny, comfortable and cheerful, with hardwood floors throughout. A Queen Anne-style house, you...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    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
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    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
    Annisquam Bridge House at Lobster Cove.1 / 32
    (3)Very good
    1.3 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Seaside Village of Lanesville - North Gloucester, MA1 / 25
    (17)Excellent
    4.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit1 / 14
    (42)Excellent
    5.8 kilometres from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    The Sand Dollar Beach House on Private Beach, easy access to all watersports.1 / 27
    (29)Excellent
    2.4 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Good Harbor Beach House1 / 23
    (127)Excellent
    5.6 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!1 / 38
    (14)Excellent
    6.0 kilometres from Wingaersheek Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    2.2 kilometres from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach1 / 21
    (40)Excellent
    6.0 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wingaersheek Beach - Newly Renovated!1 / 17
    (5)Very good
    0.7 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Historic cottage is steps from the beach on a glorious seaside estate!1 / 31
    (1)Excellent
    2.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    The Haabah--NEW!--Retreat on Good Harbor Beach1 / 49
    (5)Excellent
    5.4 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Sunset Views, Waterfront Property, Dock - Sleeps 121 / 31
    (52)Excellent
    1.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Reviewed 28 August 2017
    We had a wonderful week. Tom met us at the house and explained everything. Our daughters had a great time catching striped bass out in the Annisquam river. We took a day trip to...
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Perfect Good Harbor Beach vacation home for large and/or extended family getaway1 / 18
    (51)Excellent
    5.7 kilometres from Wingaersheek Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    Walk to Good Harbor Beach, pet friendly, family beach home1 / 22
    (43)Very good
    5.4 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Quality Accommodations in Quiet Seaside Village1 / 23
    (76)Excellent
    3.7 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak1 / 24
    (46)Excellent
    1.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    SERENITY BY THE SEA - GLOUCESTER, MA1 / 40
    (13)Excellent
    4.0 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family1 / 23
    (14)Excellent
    0.7 kilometres from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 15
    Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.1 / 25
    (18)Excellent
    2.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedroom LUX House/with Pool Next Door1 / 45
    (92)Excellent
    4.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Oceanfront Home in Estate Setting in Gloucester1 / 36
    (42)Excellent
    1.5 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    0.7 kilometres from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    6.2 kilometres from Wingaersheek Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 5 Bedrooms, 2 Bathrooms, Sleeps 8
    Magnolia Tides: Multi-level waterfront home1 / 49
    (6)Very good
    8.5 kilometres from Wingaersheek Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Two Beaches: Walk to Long Beach or Good Harbor!1 / 23
    (11)Excellent
    6.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach1 / 37
    (14)Excellent
    8.9 kilometres from Wingaersheek Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Salt Island Views: Walking distance to Good Harbor & Long Beach.1 / 20
    (4)Excellent
    6.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedroom Waterfront Unit, Vacation or Short Term Rental1 / 23
    (41)Excellent
    5.5 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA1 / 39
    (8)Very good
    5.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Beach Walk: Good Harbor Beach footbridge just steps away!1 / 12
    (34)Very good
    5.7 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
    2.9 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    4.6 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Clean Waterfront Classic Cottage with Private Beach1 / 36
    (12)Excellent
    1.0 kilometres from Wingaersheek Beach
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Central Heating
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    2.3 kilometres from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    5.6 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    About this property
    Experience river life at its best along the banks of Mill River when you stay at this spectacular waterfront rental home with exquisite water views, a large back yard, and a private tidal dock for swimming and kayaking. For the full river experience, ask us about renting a Kayak or Stand-Up...
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cedar Ledge Annisquam: Ocean views & traditional New England charm.1 / 43
    (3)Very good
    1.2 kilometres from Wingaersheek Beach
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.1 / 39
    (5)Very good
    5.6 kilometres from Wingaersheek Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Balcony
    • Washer
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    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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