
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.
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Other great holiday rentals in Massachusetts
Superhost

Home in Sturbridge
4.85 out of 5 average rating, 55 reviewsChic & Modern Studio Lakefront House with Loft
BeckyRating, 5 stars1 month ago
This was the PERFECT weekend escape. My boyfriend and I work high stress jobs in the cities and this little place and the beautiful surroundings was the perfect way to relax and get some space from the hustle and bustle.
Top guest favourite

Tiny home in Mattapoisett
4.99 out of 5 average rating, 93 reviews101 Steps to Beach/Island/Bike Path
MadelineRating, 5 stars2 weeks ago
We stayed for Memorial Day weekend. When we showed up the instructions were very clear and the place was very clean. Everything we needed was inside the home along with bikes and all of the other amenities! We had a great time and would definitely recommend staying if you’re in the area!
Guest favourite

Flat in Westford
4.93 out of 5 average rating, 89 reviewsLarge One Bedroom Apartment
HollyRating, 5 stars1 week ago
Very spacious & beautiful interior. Kitchen is amazing great for having dinner with friends. Very comfortable and beautiful surroundings
Guest favourite

Farm stay in North Andover
4.97 out of 5 average rating, 252 reviewsWinery Studio w/ Private Hot Tub,Fireplace,Tasting
NancyRating, 5 stars3 weeks ago
I loved the beautiful location, layout of the studio, and the wine tasting was excellent.
Top guest favourite

Guest house in Sandwich
5 out of 5 average rating, 16 reviewsthe Elevated Escape
AnthonyRating, 5 stars8 months ago
Allison is a dream host. We stayed at the cottage for our engagement and proposal trip and couldn’t have picked a more perfect place for it. Allison created a magical Cape Cod experience full of beautiful details including fresh flowers, relaxing hammock, chill breakfast deck, whimsical treehouse, soft bedding and wonderful kitchen with views of nature. Everything is designed with fine taste and genuine care. Line of sights flow elegantly and framed beautiful views throughout the space. She left us handwritten notes and generously prepared the space for our engagement photoshoot. We had such a peaceful and romantic time at the cottage that it felt like a sweet home away from home. We left with lots of happy memories and inspirations. Thank you Allison. We truly loved the space and would come back again in a heartbeat!
Guest favourite

Cabin in Winchendon
4.94 out of 5 average rating, 49 reviewsThe little house on Mirror Pond
SandraRating, 5 stars3 weeks ago
Michelle was an exceptional host and her little cottage was in amazingly beautiful place to be. The inside was impeccably clean, and decorated with a simple elegance. She had so many lovely touches, such as quality shampoo and soaps; Q-tips and cotton balls and hairbands available; even the best toilet paper lol!! The kitchen was equipped with every possible thing you could use, and when we couldn’t locate a blender, Michelle went out and got a brand new one and delivered it that day… which we told her she did not have to do!! If this place allowed tiny dogs, I would see if I could rent it for a whole month in the summer…Even though the weather was cool and rainy and we didn’t get to enjoy the lake, we felt nourished by the sweetness of the inside space with the beautiful window views of the lake and woods. Please do yourself a favor and go to Michelle‘s place.
Guest favourite

Flat in Fitchburg
5 out of 5 average rating, 24 reviewsRelaxing Poolside Getaway
MayraRating, 5 stars1 week ago
Great place to stay and even more when the weather is nice to enjoy the pool. Plenty of towels available for use so that is a plus. Absolutely loved having a Keurig available for coffee throughout the day. Welcome snacks were provided which was a nice.
Superhost

Guest house in Westport
5 out of 5 average rating, 3 reviewsThe Swift's Nest
AndrewRating, 5 stars2 weeks ago
We were so thankful to find Chris and Jenny's guesthouse on short notice. The Swift's Nest is a farm stay at its best, with big windows overlooking the fields and forest. Set far back from the main road, we just heard the sounds of birds at sunset and in the morning. We had a couple chilly nights and so appreciated the beautiful woodstove near the comfortable bed. The skylight in the bathroom is also a lovely detail. We hope to return in warmer weather to take advantage of the outdoor shower :) Thank you, Chris, and can't wait to visit again!
Destinations to explore
- Fitness-friendly rentals Massachusetts
- Bungalow rentals Massachusetts
- Rentals with an accessible-height bed Massachusetts
- Loft rentals Massachusetts
- Cottage rentals Massachusetts
- Farm stay rentals Massachusetts
- Rentals with a sauna Massachusetts
- Rentals with an accessible-height toilet Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Townhouse rentals Massachusetts
- Rentals with a kayak Massachusetts
- Rentals with a washing machine and dryer Massachusetts
- Cabin rentals Massachusetts
- Beachfront rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Family-friendly rentals Massachusetts
- Flat rentals Massachusetts
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- Rentals with an EV charger Massachusetts
- Rentals with a patio Massachusetts
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- Rentals with a hot tub Massachusetts
- Family-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Chalet rentals Massachusetts
- Rentals with beach access Massachusetts
- Rentals with a firepit Massachusetts
- Boutique hotel rentals Massachusetts
- Barn rentals Massachusetts
- Rentals with lake access Massachusetts
- Rentals with pools Massachusetts
- Private suite rentals Massachusetts
- Lakehouse rentals Massachusetts
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- Hotel rentals Massachusetts
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- Mansion rentals Massachusetts
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- Bed and breakfasts Massachusetts
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- Pet-friendly rentals Massachusetts
- Rentals with outdoor seating Massachusetts
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