Vacation rentals in Massachusetts

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Top-rated holiday rentals in Massachusetts

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

Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
3 – 10 Oct
4.94 out of 5 average rating, 341 reviews
Guest favourite
Cottage in Petersham
Cider House Cottage
Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.
3 – 10 Nov
4.99 out of 5 average rating, 143 reviews
Guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll through our Lavender Labyrinth and hike our 1 mile nature walk. Convenient to local skiing & golfing.
19 – 26 May
4.9 out of 5 average rating, 365 reviews

Popular amenities for Massachusetts holiday rentals

Other great holiday rentals in Massachusetts

Guest favourite
Loft in Swampscott
Gorgeous Oceanfront Penthouse
15 – 22 Nov
5.0 out of 5 average rating, 245 reviews
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
3 – 10 June
5.0 out of 5 average rating, 217 reviews
Guest favourite
Cottage in Plymouth
Stunning ocean views, stairs down to the beach
17 – 24 Feb
4.96 out of 5 average rating, 160 reviews
Guest favourite
Guesthouse in Uxbridge
Zen Inspired Private Suite with 2-mile Trail Loop
27 Oct – 3 Nov
5.0 out of 5 average rating, 113 reviews
Guest favourite
Guest suite in Uxbridge
Beautiful, Unique, & Cozy Cedar Flat
11 – 18 July
5.0 out of 5 average rating, 263 reviews
Guest favourite
Cabin in Cohasset
Lionsgate at Cohasset
17 – 24 Apr
4.92 out of 5 average rating, 277 reviews
Guest favourite
Home in Westport
Mermaid Cottage
8 – 15 Mar
4.91 out of 5 average rating, 478 reviews
Guest favourite
Guest suite in Scituate
Private Scituate Getaway - walk to harbor
4 – 11 Mar
4.91 out of 5 average rating, 170 reviews
Guest favourite
Bungalow in Dartmouth
Updated Vintage Bungalow with Incredible Views
22 – 29 Sept
4.95 out of 5 average rating, 138 reviews
Guest favourite
Guest suite in Littleton
Historic Loft with bathroom & kitchenette
18 – 25 July
4.9 out of 5 average rating, 304 reviews
Guest favourite
Guest suite in Rockport
Halibut Point State Park. Nature Lovers Retreat
11 – 18 Oct
4.99 out of 5 average rating, 601 reviews
Guest favourite
Guest suite in New Bedford
Private Comfy/Gorgeous Getaway near Park/Zoo
7 – 14 Mar
4.99 out of 5 average rating, 438 reviews

Destinations to explore