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    Stays/Destinations/United States/Massachusetts/Gloucester, MA

    Vacation rentals in Gloucester, MA

    6 independently run vacation rentals in Gloucester, MA, run by 1 local host. 2 book online on the host's own site and the rest take inquiries, with no guest service fees.

    Stays
    6
    Local hosts
    1
    Sleeps
    6 to 8
    Pet-friendly
    1
    Book online
    2

    Search live availability in Gloucester

    The Dock House

    The Dock House

    Gloucester, MA

    A waterfront home in Gloucester with a private deep-water dock, a seaside hot tub beside an outdoor fire, kayaks, a six-person Lund dinghy and captained charters on our Whaler.

    sleeps 8

    At a glance: Sleeps 8. Pets welcome (up to 2).

    Haven's read: Private and secluded. Immersed in nature. Good for groups. Good for couples. Good for families with children.

    Book direct on bookwithhaven.com

    17 Highland St

    17 Highland St

    Gloucester, MA

    Charming 3-Bedroom Home in Historic Rocky Neck—Steps from Harbor Views, Art, and Coastal Walks

    sleeps 6

    At a glance: Sleeps 6. No pets.

    Inquire on bookwithhaven.com

    The Dock House

    The Dock House

    gloucester, Massachusetts

    A unique and peaceful retreat.

    sleeps 8

    At a glance: Sleeps 8. No pets.

    Inquire on bookwithhaven.com

    The Dock House

    The Dock House

    Gloucester, MA

    Unique and Tranquil Getaway

    sleeps 8

    At a glance: Sleeps 8. No pets.

    Book direct on bookwithhaven.com

    The Dock House

    The Dock House

    gloucester, Massachusetts

    Unique and Tranquil Getaway

    sleeps 8

    At a glance: Sleeps 8. No pets.

    Inquire on bookwithhaven.com

    The Dock House

    The Dock House

    Gloucester, MA

    Unique and Tranquil Getaway

    sleeps 8

    At a glance: Sleeps 8. No pets.

    Inquire on bookwithhaven.com

    Local hosts

    Independent hosts with more than one stay here run their own booking sites. Each links to the host's site, where every home they manage is listed.

    • Anchor & Isle1 stay here

    More in Massachusetts

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    • Vacation rentals in Salem, MA

    Questions about Gloucester, MA

    How many vacation rentals in Gloucester, MA are on Haven?
    6 stays are listed in Gloucester, MA, run by 1 independent host.
    Do I pay a service fee to book a vacation rental in Gloucester, MA?
    No. Every stay here is booked or requested on the host’s own website, which charges no guest service fee. You pay the host’s nightly rate, their cleaning fee and the local taxes.
    Are there pet-friendly vacation rentals in Gloucester, MA?
    Yes. 1 of the 6 stays in Gloucester, MA lists pets as welcome. Each listing names its pet fee and limits.
    Are there vacation rentals in Gloucester, MA for large groups?
    Yes. The largest stay in Gloucester, MA sleeps 8. Capacities here run from 6 to 8 guests.
    How do I book direct in Gloucester, MA?
    Open any stay below. Most pages book online with the full price shown; a stay marked “Inquire” takes your dates and replies from the host directly. Haven adds nothing to the price.

    Updated November 6, 2026. Listings and counts come from each host's live site.

    Build a branded booking experience guests trust — from polished listing pages to seamless checkout, guest portals with a built-in digital guidebook, and stay-ready tools.

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