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Gloucester Apartment Rentals

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    Travellers to Gloucester are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in GloucesterView all 66 rentals
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    Waterfront 2 Bedroom !1 / 42
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 19
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed 24 November 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
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    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in East Gloucester, Massachusetts wake up in a dramatic furnished waterfront 2 bedroom and one bathroom apartment living at the edge of Gloucester's Inner Harbor. The unit has hardwood floors with an open concept living with cathedral ceilings and windows galore ! Watch the sunset from a...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Close to Half Moon Bay1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 3, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming condominium is located on the ground floor of a coastal Victorian era complex. Overlooking Smith Cove and Gloucester Harbor, this romantic getaway is tastefully furnished, boasting a private patio where you can take in the views of the active port. Enter the property from the patio...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Captain John Stephens House: Sparkling new studio in the heart of Gloucester1 / 24
    (1)Average
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2017
    When we walked into the rental, it was nicely decorated and very clean, but there were hidden problems. No air conditioning, and the damage deposit is nonrefundable. Had to...
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    About this property
    Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual or couple...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2018! Indulge in luxury at Diamond in the Sky. Gleaming floors, elegant decor, central air, an incredible roof deck, ocean views and even an elevator, this brand new townhouse has everything for the perfect beach getaway. Inside, this sun-drenched vacation home is beautifully decorated...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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