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Vacation Rentals near Wingaersheek Beach

Gloucester, Massachusetts
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    Travelers to Gloucester are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 192 Rentals in Gloucester
    Steps to Wingaersheek's Private 1.5 Mile White Dune Beach1 / 17
    0.7 miles from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)1 / 24
    1.7 miles from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Seaside Village of Lanesville - North Gloucester, MA1 / 25
    (17)Excellent
    2.7 miles from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit1 / 30
    (52)Excellent
    3.6 miles from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Gloucester, Cape Ann
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Ocean and Woods! Best of both seaside delights in Gloucester!1 / 21
    3.9 miles 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
    The Haabah Beach Retreat—4 Minute Walk to Beach1 / 30
    (5)Excellent
    3.8 miles from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunset Views, Waterfront Property, Dock - Sleeps 121 / 30
    (11)Excellent
    0.8 miles from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Bring your fishing gear!
    Reviewed August 27, 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Spectacular Sunsets And Private Beach In A Nantucket Style Summer Cottage.1 / 30
    1.6 miles from Wingaersheek Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil1 / 30
    3.9 miles from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Gloucester, Cape Ann
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 15
    Walk to Good Harbor Beach, pet friendly, family beach home1 / 22
    (46)Very good
    3.4 miles from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury Accommodations in Quiet Seaside Village1 / 23
    (87)Excellent
    2.3 miles 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
    (49)Excellent
    0.7 miles from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI1 / 23
    (10)Excellent
    3.2 miles from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.1 / 30
    (18)Excellent
    1.5 miles from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedroom LUX House/with Pool Next Door1 / 30
    (109)Excellent
    2.7 miles from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE1 / 30
    (44)Excellent
    1.2 miles from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Gloucester, Cape Ann
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES1 / 30
    (13)Excellent
    0.7 miles 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
    Good Harbor Beach House1 / 30
    (136)Excellent
    3.5 miles from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!1 / 30
    (14)Excellent
    3.7 miles 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
    Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas1 / 30
    1.3 miles from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Gloucester, Cape Ann
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Large, open floor plan. Water views of Lanes Cove. Walk to Plum Cove beach.1 / 15
    2.3 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach1 / 21
    (12)Excellent
    3.7 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Historic cottage is steps from the beach on a glorious seaside estate!1 / 30
    (4)Excellent
    1.3 miles from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Walk to Good Harbor Beach 6/10 mile.1 / 8
    3.5 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Perfect Good Harbor Beach vacation home for large and/or extended family getaway1 / 18
    (5)Excellent
    3.5 miles from Wingaersheek Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Gloucester, Cape Ann
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam1 / 24
    (28)Excellent
    0.3 miles from Wingaersheek Beach
    6 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    Gloucester, Cape Ann
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 15
    Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family1 / 30
    (21)Excellent
    0.4 miles from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Gloucester, Cape Ann
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 15
    A tranquil ocean retreat steps from the water's edge1 / 13
    (7)Excellent
    2.6 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Harbor View House, Walk to Beach, Sunsets from Deck1 / 30
    3.4 miles from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Unobstructed, Direct Ocean Views! Walk to Good Harbor!1 / 30
    4.0 miles from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Magnolia Tides: A gracious and luxurious multi-level waterfront home.1 / 30
    (6)Very good
    5.2 miles from Wingaersheek Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Downtown Dahlias fully remodeled in the heart of Gloucester1 / 30
    2.7 miles from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Two Beaches: Walk to Long Beach or Good Harbor!1 / 30
    (11)Excellent
    3.8 miles from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Salt Island Views: Walking distance to Good Harbor & Long Beach.1 / 30
    (4)Excellent
    3.8 miles from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    DRIFT Accommodations, Perfect Location1 / 20
    (3)Excellent
    3.2 miles from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Lovely 2br Cherry apt in Gloucester/Free parking/king bed1 / 26
    1.9 miles from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
    BEACH! Good Harbor NEW CONSTRUCTION!!!!1 / 27
    3.5 miles from Wingaersheek Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly1 / 26
    (8)Very good
    3.2 miles from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks1 / 22
    3.7 miles from Wingaersheek Beach
    Studio, 2 Bathrooms, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bathrooms, Sleeps 4
    Coastal condo with easy beach access, board games, jetted tub, W/D, and AC1 / 22
    3.9 miles from Wingaersheek Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Ocean Breeze / King Bed / 8-Minute Walk to Beach1 / 20
    3.5 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Seaside Escape just steps to Good Harbor beach in Gloucester1 / 22
    3.4 miles from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Romantic Summerwind Cottage, Harbor View w/Large Deck1 / 30
    (10)Excellent
    3.4 miles from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Location Information
    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Waterfront Woodsy 3BR Cottage1 / 68
    (1)Excellent
    2.7 miles from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Yard
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    Charming, well-located older cottage by the sea
    Reviewed August 28, 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    NEW Oceanside Village Home~Private Fenced Yard~Reserved Parking1 / 23
    2.5 miles from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Location Information
    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Steps to Harbor, Park, Beach and Boardwalk1 / 18
    3.0 miles from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    NEW 3BR/2 BA Harborside Home . Backyard+Grill . Ocean Views1 / 20
    3.6 miles from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Sunset Cove: Waterfront home in Goose Cove section of Gloucester.1 / 30
    (10)Very good
    0.8 miles from Wingaersheek Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Gloucester, Cape Ann
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Enjoy the ambiance of a New England Seaside Getaway, without the crowds!1 / 23
    3.7 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Location Information
    Gloucester, Cape Ann
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Walk to Good Harbor Beach and Downtown Gloucester1 / 14
    3.4 miles from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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