
Guesthouse vacation rentals in Massachusetts
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Top-rated guesthouse rentals in Massachusetts
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts guesthouse rentals
Family-friendly guest house rentals

Amherst Area Studio Apartment

The East Street Cabin

Large Studio – Walk to Town

Abundant Blessings Cottage – Wellfleet

Country Cottage in the City

Light-filled North Truro cottage-Lovely gardens

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Beautiful Guest House in Chilmark
Guest house rentals with a patio

Charming Guesthouse with Access to Private Beach

Private 1 king bedroom guest house-2021 built

Waterfront Cottage / Your Cape Escape

Jimmy & Donny's AirBnB

Two Penny Loft at Amesbury Farmhouse - Guest Suite

Claw Foot Tub & King Bed at Club Tanuki Cottage

the Elevated Escape

One BD In-law with Private Ent.
Guest house rentals with a washer and dryer

Light-filled Carpenter's Cottage in Stockbridge

Cute mill house: 3BR•Wood stove *Brkfst included*

Lovely & Spacious 2 BR (W/King/Queen beds) 2 Bath

Spacious Suite 15 mi from Boston

Vineyard Meadow Artist Studio

Modern barn in the heart of the Berkshires

Adorable Vineyard Haven Cottage

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