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Gloucester: Vacation Rental By Owner

Search result 1 to 20 Of 52
  • Property-1 Image 1
    House Select Dates for Price
    • 2Bed
    • 1Baths
    • (25) Exceptional
    Gloucester, MA

    As you arrive at Serenity, you're welcomed by a beautifully maintained neighborhood. Then you entire a meticulously maintained home. The dining area and... ...more

  • Property-2 Image 1
    Guest House $562 / Nightly
    • 1Bed
    • 1Baths
    • (8) Exceptional
    Gloucester, MA

    Relax at "SERENITY BY THE SEA" a brand new apartment on the ocean in Gloucester, MA. Spectacular sunsets are enjoyed every night in the living room, or out on the... ...more

  • Property-3 Image 1
    Cottage $280 / Nightly
    • 1Bed
    • 1Baths
    • (36)
    Gloucester, MA

    This quaint 1900's cottage was completely renovated in 2006. It has seasonal ocean views and Plum Cove beach is just 500 ft away! The full gourmet kitchen has... ...more

  • Property-4 Image 1
    Cottage $474 / Nightly
    • 2Bed
    • 1Baths
    • (21) Wonderful
    Gloucester, MA

    Enjoy the beauty of Cape Ann at this romantic three season cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back... ...more

  • Property-5 Image 1
    House $269 / Nightly
    • 2Bed
    • 2Baths
    • (28)
    Gloucester, MA

    Delightful 8 room romantic, colonial home on beautifully landscaped lot just 5 doors from Plum Cove Beach. Get away from it all and watch the spectacular sunsets... ...more

  • Property-6 Image 1
    House $714 / Nightly
    • 5Bed
    • 3Baths
    • (41) Wonderful
    Gloucester, MA

    Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms,... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 4Bed
    • 2Baths
    • (23) Excellent
    Gloucester, MA

    This shingled house sits atop a rocky hill overlooking picturesque Diamond Cove, in Annisquam. Our house has postcard seascape views from both porches and every... ...more

  • Property-8 Image 1
    House $330 / Nightly
    • 3Bed
    • 3Baths
    • (27) Wonderful
    Gloucester, MA

    This lovely, tastefully decorated 3 BR home is 4/10 mile from the soft sands of spectacular Good Harbor Beach. Whether taking a morning walk or packing a cooler... ...more

  • Property-9 Image 1
    House $793 / Nightly
    • 6Bed
    • 4Baths
    • (12) Exceptional
    Gloucester, MA

    This is the vacation house you have been looking for! It’s perfectly located only a few steps from the private & secluded section of Coffins Beach. As well as a... ...more

  • Property-10 Image 1
    House $390 / Nightly
    • 4Bed
    • 3Baths
    • (16)
    Gloucester, MA

    The Ledge House is a charming mid 19th century farmhouse situated below a large granite ledge in the village of Bay View in Gloucester, MA. The beauty of the... ...more

  • Property-11 Image 1
    House $891 / Nightly
    • 5Bed
    • 2Baths
    • (11) Wonderful
    Gloucester, MA

    Open and bright, fully furnished 5 bedroom, 2 bathroom house literally a few steps away from Good Harbor Beach, one of the nicest, cleanest and most highly rated... ...more

  • Property-12 Image 1
    House $437 / Nightly
    • 5Bed
    • 2Baths
    • (5) Wonderful
    Gloucester, MA

    Step back in time, this Antique colonial (circa 1746) offers a large place to spend time with family and friends. With lot's of place to sleep and chat. The... ...more

  • Property-13 Image 1
    House $673 / Nightly
    • 3Bed
    • 3Baths
    • (12) Excellent
    Gloucester, MA

    Relax at the scenic New England coastline at Diamond Cove. Access 2 member beaches within walking distance. Experience the most breathtaking sunsets on the East... ...more

  • Property-14 Image 1
    Apartment $222 / Nightly
    • 1Bed
    • 1Baths
    • (87) Wonderful
    Gloucester, MA

    1 small, non-shedding dog (under 15 lbs) will be considered, PLEASE INQUIRE BEFORE BOOKING WITH PET. Nestled on a hillside overlooking E. Gloucester's scenic... ...more

  • Property-15 Image 1
    House $434 / Nightly
    • 3Bed
    • 3Baths
    • (71)
    Gloucester, MA

    WELCOME From this convenient in-town location enjoy restful refinement while also delighting in being part of the Gloucester experience. This 2800 sq ft,... ...more

  • Property-16 Image 1
    House $680 / Nightly
    • 8Bed
    • 2Baths
    • (25)
    Gloucester, MA

    Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your life. The home is situated between two of... ...more

  • Property-17 Image 1
    House $757 / Nightly
    • 3Bed
    • 3Baths
    • (6) Exceptional
    Gloucester, MA

    Fully Air conditioned (New May 2017!) spacious beach house with views from almost every room --3 bedroom/3 bath home stylishly furnished with your beach vacation... ...more

  • Property-18 Image 1
    House $197 / Nightly
    • 3Bed
    • 3Baths
    • (86)
    Gloucester, MA

    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... ...more

  • Property-19 Image 1
    Condo $397 / Nightly
    • 3Bed
    • 3Baths
    • (1) Exceptional
    Gloucester, MA

    This newly renovated 3 level, 3 bedroom, 2.5 baths, fully stocked beach condo, also has 3 outdoor patio areas, and parking for 3 cars. Indoor features include 3... ...more

  • Property-20 Image 1
    House $223 / Nightly
    • 2Bed
    • 2Baths
    Gloucester, MA

    Two story, 3 bedroom, 1 1/2 bath located right over the bridge in the seaside town of Gloucester. With eat in kitchen, open dining room- living room, and one... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Gloucester. Many accommodations in Gloucester provide "Non Smoking Only", there are 124, or there are 104 of Vacation Rentals in Gloucester with a "Pets Not Allowed", there are also 102 with "Fishing", which is another great reason to visit Gloucester.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Gloucester. The most expensive month of the next 12 months is in January, where prices hit an average of $428 a night. In , prices will hit an average low of $0 per night.