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Pet Friendly Holiday Rentals in Gloucester

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    R 6 002 Average
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    Travellers to Gloucester are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    12 Matching Rentals in GloucesterView all 65 rentals
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 25
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Dragonfly1 / 7
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living room with plenty...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two full bath home that boasts a...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    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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    01930, Gloucester, Cape Ann
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is close to walk to or short drive to restaurants and dining, family-friendly activities, the beach, nightlife, whale watching . You’ll love my place because of the coziness , the comfy bed, the relaxed and easy atmosphere, and close proximity to all Gloucester, Rockport and Cape Ann have...
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    01930, Gloucester, Cape Ann
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and living...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester with easy access to highway....
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Patio
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront tri-level, with 4 bedrooms, 2 full baths, fire pit and a dock will accommodate up to 10 people. Located on Little River, a tidal inlet, just off the Annisquam River, we have water access mostly all day. The yard, screened porch and patio face west for the most spectacular sunsets. The...
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    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that flank the front door from which you may also enjoy the views of the sunrise. On a clear day,...
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    Location Information
    01930, Gloucester, Cape Ann
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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