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Vacation Rentals nearby Wingaersheek Beach

Gloucester, Massachusetts
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    Travellers to Gloucester are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 180 Rentals in Gloucester
    1.1 kilometres from Wingaersheek Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES1 / 30
    (5)Excellent
    1.2 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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 / 30
    (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 / 30
    (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
    3.7 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
    Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach1 / 21
    (12)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
    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
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    Historic cottage is steps from the beach on a glorious seaside estate!1 / 30
    (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 Beach Retreat—4 Minute Walk to Beach1 / 30
    (4)Excellent
    6.1 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
    Sunset Views, Waterfront Property, Dock - Sleeps 121 / 30
    (7)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
    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
    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
    6.3 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
    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
    Luxury Accommodations in Quiet Seaside Village1 / 23
    (87)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
    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 15 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 15
    Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI1 / 23
    (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
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    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 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    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 / 30
    (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
    Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE1 / 30
    (3)Excellent
    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
    A tranquil ocean retreat steps from the water's edge1 / 13
    (1)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
    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
    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
    4.4 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Two Beaches: Walk to Long Beach or Good Harbor!1 / 30
    (8)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 / 30
    (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
    DRIFT Accommodations, Perfect Location1 / 20
    (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
    Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA1 / 30
    (4)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
    0.9 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
    3.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    3.1 kilometres 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
    4.9 kilometres from Wingaersheek Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    4.6 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Clean Waterfront Classic Cottage with Private Beach1 / 30
    (5)Very good
    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
    2.3 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
    5.5 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    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
    Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.1 / 30
    (5)Very good
    5.6 kilometres from Wingaersheek Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly1 / 26
    (6)Very good
    5.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    5.9 kilometres from Wingaersheek Beach
    Studio, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Waterfront
    • Internet Access
    • Skiing: Property Is In A Ski Resort
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 2 Bathrooms, Sleeps 4
    1.9 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Walk to Good Harbor and Long Beach -Vacation Home1 / 29
    (2)Average
    6.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Grill
    • Air Conditioning
    • Terrace
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    5.7 kilometres from Wingaersheek Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1
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