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Gloucester Cheap Rentals

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    Travelers to Gloucester are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    17 Matching Rentals in GloucesterView all 69 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky shores and seafood markets. Dive...
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    Gloucester, Cape Ann 01930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 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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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    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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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed January 27, 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The dining area and deck overlook a gardeners delight of perpetually blooming flowers surrounding a Koi pond a beautiful woodsy backdrop - the backyard is a slice of heaven, and yours to enjoy when you stay at Serenity. This home is nestled in a quiet neighborhood surrounded by attractions like...
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    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Balcony
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    Mark's rental apartment in Gloucester is my all-time favorite rental home! It offers a comfortable queen-sized bed, an additional bedroom with a twin, a living room with a small...
    Reviewed October 5, 2017
    When we arrived our host met us at the door and let us in, the first thing we noticed was the wonderful view and a balcony to sit on. We were close to most places by walking.
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    About this property
    Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern comfort meets colonial charm at this gorgeous home on the banks of Lobster Cove. Beautifully designed, with a gourmet kitchen and abundant skylights and windows that gaze out onto tranquil views of the water, this updated house offers coziness and elegance in equal measure. A quiet...
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    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Close to Half Moon Bay1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Grill
    • Terrace
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    • 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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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Patio
    • Waterfront
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come together with your friends and family for the trip of a lifetime at this Gloucester vacation rental cottage for 12! Three bedrooms, 1.5 bathrooms, plus a detached log cabin, create the perfect retreat - where you'll be ruled by the ocean's high and low tides and unforgettable sunrises and...
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    Gloucester, Cape Ann 01930
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art...
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    Gloucester, Cape Ann 01930
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern one bedroom apartment with a new kitchen and updated bathroom, inside our contemporary home above Good Harbor beach. Privately separated with the front door as the main entrance. Open concept kitchen+ living room with dining seating for 6! Cool place to rest after a long day at the...
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    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 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 November 24, 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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    Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.1 / 17
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 2016
    everything about this place was A+ ,the owners ,the apartment ,the location,the scenery,everything was awesome
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    About this property
    Welcome, cher ami ('dear friend'), to this gleaming second-floor vacation rental. Cher Ami is available as a summer rental and an off-season rental. Cher Ami is a spacious and sunny apartment, with 2 bedrooms plus an office space, an eat-in kitchen with an island, 2 bedrooms plus an office...
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    Location Information
    Gloucester, Cape Ann 01930
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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