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Holiday Rentals nearby Wingaersheek Beach

Gloucester, Massachusetts
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    ₹53,229 Average
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    Travellers to Gloucester are booking June dates now. Secure your holiday home today, and have the perfect trip.
    All 21 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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    5.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    5.2 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    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
    1.3 kilometres from Wingaersheek Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Washer
    • 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
    2.8 kilometres from Wingaersheek Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Patio
    • Grill
    • Balcony
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    • Central Heating
    Suitability
    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
    2.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
    • Terrace
    • Balcony
    • Wi-Fi
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    • Grill
    • DVD Player
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    Suitability
    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 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
    1.2 kilometres from Wingaersheek Beach
    6 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Smoking allowed
    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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    • Grill
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    2.0 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Waterfront
    • Wi-Fi
    • Washer
    Suitability
    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
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    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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    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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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    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 30 August 2020
    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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    Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Waterfront Woodsy 3BR Cottage1 / 68
    (1)Excellent
    4.4 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    3.7 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Exquisitely renovated by the owner-architect, every detail of this charming vacation home has been thoughtfully considered. Located in an American Foursquare home on a quiet dead end street, it's backyard fronts the Annisquam River. Relax on the deck and watch the boats or launch a kayak in at high...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, 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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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    • Wi-Fi
    • DVD Player
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air...
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    Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.3 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy casual and carefree living in West Gloucester this summer! Just a half mile from Wingaersheek Beach, this simple single-story cottage awaits your arrival. The living room’s cathedral ceiling lends an airy feel to the space and your eyes will be riveted to the windows that offer a surprising...
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    Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    4.4 kilometres from Wingaersheek Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come Escape to our Waterfront Retreat **Currently, we have availability open in June 2021. Booked all of July and August.** The Rockwood Lodge is the perfect place to step away from the hustle and bustle of everyday life. Some 15 yards from the waterline of beautiful Ipswich Bay, this two-story...
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    Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    5.1 kilometres from Wingaersheek Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Rockport Village, Captain John Butman House is steeped in history, originating in the days before the United States of America came to be. With its strong colonial bones, this delightful rental home was lovingly restored and refinished with modern upgrades while maintaining its historic...
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    Rockport, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5.1 kilometres from Wingaersheek Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just up the street from Rockport's beautiful Front Beach, this charming 2-bedroom vacation rental is newly renovated reflecting the simple and soft coastal hues in its interior decor. With its close proximity to the town's beaches, parks, and many attractions, The Cottage at Front Beach is...
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    Rockport, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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