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Holiday 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
1–8 SeptIndividual Host,
£352 per night
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.
17–24 JunIndividual Host,
£135 per night
4.99 out of 5 average rating, 143 reviews
Guest favourite
Bungalow in Dartmouth
Updated Vintage Bungalow with Incredible Views
This space has been fully updated in the spring of 2020. Incredible unobstructed panoramic views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stones throw from I-195, making places like Boston, Providence and the Cape and Islands very easy to get to. The décor is bright and funky! Close to UMASS. Extensive custom area and house guide is at the Bungalow with everything you need to know to maximize your experience in the area!
14–21 MarIndividual Host,
£124 per night
4.95 out of 5 average rating, 138 reviews

Popular amenities for Massachusetts holiday rentals

Other great holiday rentals in Massachusetts

Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
3–10 JunIndividual Host,
£274 per night
5.0 out of 5 average rating, 216 reviews
Guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
12–19 May
£141 per night
4.9 out of 5 average rating, 365 reviews
Guest favourite
Guest house in Uxbridge
Zen Inspired Private Suite with 2-mile Trail Loop
24–31 Aug
£135 per night
5.0 out of 5 average rating, 113 reviews
Guest favourite
Guest suite in Uxbridge
Beautiful, Unique, & Cozy Cedar Flat
19–26 AugIndividual Host,
£125 per night
5.0 out of 5 average rating, 262 reviews
Guest favourite
Loft in Swampscott
Gorgeous Oceanfront Penthouse
1–8 JunIndividual Host,
£320 per night
5.0 out of 5 average rating, 244 reviews
Guest favourite
Cottage in Plymouth
Stunning ocean views, stairs down to the beach
22–29 SeptIndividual Host,
£352 per night
4.96 out of 5 average rating, 160 reviews
Guest favourite
Cottage in Sandwich
Lil’ Sea Sass ~ Oceanfront Cottage & Pet Friendly
7–14 FebIndividual Host,
£520 per night
4.88 out of 5 average rating, 295 reviews
Guest favourite
Home in Mattapoisett
*Cozy Escape* Historic South Coast Retreat
11–18 NovIndividual Host,
£128 per night
4.94 out of 5 average rating, 122 reviews
Guest favourite
Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
28 Jul – 4 AugProfessional Host,
£264 per night
4.95 out of 5 average rating, 182 reviews
Guest favourite
Cabin in Cohasset
Lionsgate at Cohasset
9–16 MarIndividual Host,
£107 per night
4.92 out of 5 average rating, 277 reviews
Guest favourite
Guest house in Barnstable
Modern Fireplaced Carriage House with Beach Permit
5–12 May
£328 per night
5.0 out of 5 average rating, 109 reviews
Superhost
Farm stay in Southbridge
Scandanavian Wigwam with Sauna and Forest Baths
14–19 MayIndividual Host,
£152 per night
4.88 out of 5 average rating, 280 reviews

Destinations to explore