Gloucester: Vacation Rental By Owner

Showing 20 Of 56 Vacation Rentals
  • Property-1 Image 1
    Apartment $222 / Nightly
    • 1 Bed
    • 1 Baths
    • (85)
    Gloucester, MA

    Nestled on a hillside overlooking E. Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from... ...more

  • Property-2 Image 1
    Apartment Select Dates for Price
    • 3 Bed
    • 1 Baths
    • (25) Wonderful
    Gloucester, MA

    Perfectly located turn of the century Bayview home is nestled between Annisquam Village and Lanesville… a short walk to Plum Cove Beach or if you prefer just... ...more

  • Property-3 Image 1
    House Select Dates for Price
    • 4 Bed
    • 2 Baths
    • (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-4 Image 1
    Cottage $228 / Nightly
    • 1 Bed
    • 1 Baths
    • (17) Wonderful
    Gloucester, MA

    Please enjoy our fully renovated one bedroom, one bathroom cottage. It is a 5 minute walk to Long Beach, less a than 10 minute walk to Good Harbor Beach. Enjoy... ...more

  • Property-5 Image 1
    House Select Dates for Price
    • 3 Bed
    • 3 Baths
    • (11)
    Gloucester, MA

    My husband and I want to assure you that we take your family's health and safety very seriously. Our house is professionally cleaned after each guest, to ensure... ...more

  • Property-6 Image 1
    House $891 / Nightly
    • 5 Bed
    • 2 Baths
    • (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-7 Image 1
    House Select Dates for Price
    • 3 Bed
    • 3 Baths
    Gloucester, Massachusetts

    New Property for 2020. Plaisance is a comfortable modern home nestled in a quiet, leafy neighborhood not far from Good Harbor Beach and the Bass Rocks Golf... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (2) Very Good
    Gloucester, MA

    Located right around the corner from Gloucester’s fabled Stacy Boulevard, this completely renovated vacation rental home provides convenient access to downtown... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (5) Exceptional
    Gloucester, MA

    Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to... ...more

  • Property-10 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (2) Exceptional
    Gloucester, MA

    Picture yourself on the huge wraparound deck of Ships Bell House, enjoying the setting of the sun over breathtaking water views. That's the moment you'll never... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    Gloucester, Massachusetts

    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... ...more

  • Property-12 Image 1
    House $680 / Nightly
    • 8 Bed
    • 2 Baths
    • (42) Excellent
    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-13 Image 1
    House $714 / Nightly
    • 5 Bed
    • 3 Baths
    • (42) 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-14 Image 1
    House Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (25) Exceptional
    Gloucester, MA

    Are you ready for a quick get-away? Good news! Massachusetts has opened Short-Term rentals as of June 8th. Please feel free to book your vacation. When you... ...more

  • Property-15 Image 1
    Guest House $562 / Nightly
    • 1 Bed
    • 1 Baths
    • (10) Exceptional
    Gloucester, MA

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

  • Property-16 Image 1
    House $349 / Nightly
    • 4 Bed
    • 2 Baths
    • (30)
    Gloucester, MA

    Stunning sunsets, a parade of boats going by, a charming marina, and a beach brimming with natural beauty — these are the sights you’ll behold at this year-round... ...more

  • Property-17 Image 1
    Guest House $207 / Nightly
    • 1 Bed
    • 1 Baths
    • (14)
    Gloucester, MA

    Sunny and bright the cottage sits on a private quarry and is waiting for you to come enjoy all Cape Ann has to offer. Enjoy reading, relaxing, and swimming in the... ...more

  • Property-18 Image 1
    House $197 / Nightly
    • 3 Bed
    • 3 Baths
    • (112) Wonderful
    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
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (18)
    Gloucester, MA

    Cozy house located 1 street back from the Boulevard on Gloucester Harbor. Sunny, bright and cheery house with a sitting area outside. House is one of 4 on a... ...more

  • Property-20 Image 1
    Guest House $511 / Nightly
    • 3 Bed
    • 3 Baths
    • (2) Exceptional
    Gloucester, MA

    Beautiful beach house located DIRECTLY on the Good Harbor Estuary, overlooking Good Harbor Beach. The house is close enough to the ocean (4 min walk to the sand)... ...more

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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 July, where prices hit an average of $271 a night. In June, prices will hit an average low of $350 per night.