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Vacation Rentals nearby Wingaersheek Beach

Gloucester, Massachusetts
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    Travellers to Gloucester are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 152 Rentals in Gloucester
    Steps to Wingaersheek's 1.5 Mile White Dune Private Beach1 / 14
    (2)Excellent
    1.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    5.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annisquam Bridge House at Lobster Cove. Booking fall/winter1 / 29
    (13)Excellent
    1.2 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 / 24
    (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 / 29
    (52)Excellent
    5.8 kilometres from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Good Harbor Beach House1 / 29
    (136)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 / 29
    (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
    Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas1 / 27
    (7)Excellent
    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 / 20
    (50)Excellent
    6.0 kilometres from Wingaersheek Beach
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Wingaersheek Beach - Newly Renovated!1 / 16
    (11)Excellent
    0.7 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    Ocean and Woods! Best of both seaside delights in Gloucester!1 / 20
    (17)Excellent
    6.4 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
    Historic cottage is steps from the beach on a glorious seaside estate!1 / 29
    (4)Excellent
    2.1 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 / 29
    (5)Excellent
    5.7 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Sunset Views, Waterfront Property, Dock - Sleeps 121 / 29
    (56)Excellent
    1.3 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    2.6 kilometres from Wingaersheek Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Waterfront
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5.6 kilometres 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 / 17
    (56)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
    Long Beach Private & Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil1 / 29
    (11)Excellent
    6.3 kilometres from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 6
    Walk to Good Harbor Beach, pet friendly, family beach home1 / 22
    (46)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
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    Luxury Accommodations in Quiet Seaside Village1 / 22
    (87)Excellent
    3.7 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
    Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam1 / 24
    (28)Excellent
    0.5 kilometres from Wingaersheek Beach
    6 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 6
    BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak1 / 24
    (49)Excellent
    1.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 3
    Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI1 / 22
    (10)Excellent
    5.1 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
    Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family1 / 29
    (21)Excellent
    0.7 kilometres from Wingaersheek Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 6
    Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.1 / 24
    (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 / 29
    (109)Excellent
    4.4 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    2.0 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
    2.5 kilometres from Wingaersheek Beach
    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
    5.5 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    A tranquil ocean retreat steps from the water's edge1 / 12
    (76)Excellent
    4.3 kilometres 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
    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
    6.5 kilometres 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 / 29
    (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
    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
    Two Beaches: Walk to Long Beach or Good Harbor!1 / 22
    (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
    Salt Island Views: Walking distance to Good Harbor & Long Beach.1 / 19
    (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
    5.5 kilometres from Wingaersheek Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    DRIFT Accommodations, Perfect Location1 / 19
    (3)Excellent
    5.2 kilometres 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
    Beach Walk: Good Harbor Beach footbridge just steps away!1 / 11
    (34)Very good
    5.7 kilometres 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
    Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA1 / 29
    (13)Very good
    5.4 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 5
    4.6 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    2.3 kilometres from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 5
    5.6 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Clean Waterfront Classic Cottage with Private Beach1 / 29
    (15)Excellent
    1.2 kilometres from Wingaersheek Beach
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Cedar Ledge Annisquam: Ocean views & traditional New England charm.1 / 29
    (5)Very good
    1.2 kilometres from Wingaersheek Beach
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    5.5 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    3.8 kilometres from Wingaersheek Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
    5.6 kilometres from Wingaersheek Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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