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    Stays/Destinations/United States/Massachusetts/With a story

    Vacation rentals with a story in Massachusetts

    4 independently run vacation rentals with a story in Massachusetts. 4 sleep 8 or more, 4 are quiet, 1 is surrounded by nature. Book direct on each host's own site, with no guest service fees.

    Stays
    4
    Sleeps
    8 to 12
    Pet-friendly
    1

    Search live availability

    • Quiet4
    • Condos2
    • Cottages2
    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

    2 Mi to Wychmere, 3 King Beds, Fenced-in, FirePit

    2 Mi to Wychmere, 3 King Beds, Fenced-in, FirePit

    Harwich, MA

    Charming cottage near beaches and trails.

    sleeps 8

    At a glance: Sleeps 8. No pets.

    Book direct on bookwithhaven.com

    Villaggio by the Sea

    Villaggio by the Sea

    Beverly, MA

    Escape to a Cozy, Scenic Retreat by the Sea.

    sleeps 8

    At a glance: Sleeps 8. No pets.

    Book direct on bookwithhaven.com

    Historic Brick Mansion

    Historic Brick Mansion

    Salem, MA

    Federal Period brick mansion on fabled Chestnut Street

    sleeps 12

    At a glance: Sleeps 12. No pets.

    Book direct on bookwithhaven.com

    More in Massachusetts

    • All vacation rentals in Massachusetts
    • Vacation rentals with a story everywhere on Haven

    Questions about Massachusetts

    How many vacation rentals with a story in Massachusetts are there?
    4 stays in Massachusetts qualify. Each has a provenance of its own, a history, a conversion, a working farm or a family legacy, noted by Haven’s curator.
    What makes a stay count as vacation rental with a story?
    Each has a provenance of its own, a history, a conversion, a working farm or a family legacy, noted by Haven’s curator. The rule is the same for every stay, so a page never lists one on a guess.
    Do I pay a service fee to book vacation rentals with a story in Massachusetts?
    No. Every stay here is booked or requested on the host’s own website, which charges no guest service fee.
    How many guests do these vacation rentals with a story sleep?
    From 8 to 12 guests, listed on each card.

    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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