Vacation rentals in Massachusetts

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Top-rated vacation rentals in Massachusetts

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room · Milford
Quiet Red Room in Milford
Very quiet neighborhood. Nice place to rest or study
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Tiny homes · Orange
The Writer's Retreat: A Sweetwater Stay
Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.
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Treehouse · Lee
Gingerbread House Tower in the Berkshire Hills
Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.
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Other great vacation rentals in Massachusetts

Entire chalet · Otis
Octagonal Glass Treehouse in Berkshires
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Tiny homes · Lee
Enchanted Tiny Tower nestled in the Berkshires
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Entire cottage · Pittsfield
The Guest House at Cottage Farm
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Hotel room · Hull
Nantasket Beach Resort - Two Queen Ocean View
Entire home · Plymouth
Historic 1 Bed/In Town/Best Location/Hot tub/deck
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Treehouse · New Marlborough
Double 3 Bedroom Tree House in the Berkshires
Private room · Waltham
Nicely Decorated in Boston Suburb- Green Room
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Entire cottage · Orange
The Lake Cottage: A Sweetwater Stay
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Entire home · Plymouth
Ocean Side, Amazing View, close to town/beach, Spa
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Entire cottage · Ashburnham
Lakeside cottage, "Breezy Point"
Entire home · Dennis
The America House
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Private room · Chelsea
Private, Intimate Ocean Blue Room @ The Washburn!
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