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Resort holiday rentals in Massachusetts
Find and book unique resort stays on Airbnb
Top-rated resort stays in Massachusetts
Guests agree: These resort stays are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts resort stays
Family-Friendly Resort Stays
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Private room in Brewster
4.32 out of 5 average rating, 82 reviewsOcean Edge Resort One Bedroom Villa
![](https://a0.muscache.com/im/pictures/f32c8102-1751-4ebd-9b4a-8c8dd61daa77.jpg?im_w=720)
Hotel room in Brewster
4.46 out of 5 average rating, 56 reviewsOcean Edge Resort One Bedroom Villa
![](https://a0.muscache.com/im/pictures/5ba7f10d-d51c-40e3-88f2-c18b3e3aef21.jpg?im_w=720)
Resort in Dennis
4.75 out of 5 average rating, 4 reviewsBeachfront 1 BR Suite, Dennis Port July 12 - 19
![](https://a0.muscache.com/im/pictures/c177004c-c2fb-421f-9094-2422f0de4e38.jpg?im_w=720)
Private room in Dennis
4.6 out of 5 average rating, 5 reviewsOcean front 2-bedroom suite on beautiful beach
![](https://a0.muscache.com/im/pictures/90462019-3e90-4f19-8bd1-1ed172edf4a8.jpg?im_w=720)
Private room in Brewster
4.53 out of 5 average rating, 47 reviewsOcean Edge Resort One Bedroom Condo
Resort rentals with a pool
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-42971022/original/bff050b8-936a-45f5-8b6d-cbdaabcef064.jpeg?im_w=720)
Private room in Chatham
5 out of 5 average rating, 15 reviewsPleasant Bay Village Resort - Extra Deluxe Queen
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-43767854/original/68c85aa3-fa43-4302-a762-8ddc754673b2.jpeg?im_w=720)
Private room in Chatham
5 out of 5 average rating, 3 reviewsLower Deluxe Two Bedroom Cottage
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-43372551/original/a8746d6a-dc15-4664-b8b8-1d21b50ab8e4.jpeg?im_w=720)
Private room in Chatham
5 out of 5 average rating, 7 reviewsUpper Deluxe Two Bedroom Cottage
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-42971024/original/293835b0-63d8-4f5b-a847-93686f657b66.jpeg?im_w=720)
Private room in Chatham
4.88 out of 5 average rating, 17 reviewsPleasant Bay Village Resort - Rear Deluxe Studio
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-43767853/original/05c5bf4d-125f-44c2-af5c-876edea8e117.jpeg?im_w=720)
Private room in Chatham
One Bedroom Cottage Suite
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-43767852/original/a08a632c-9732-407b-a89c-6b9f1db5bf22.jpeg?im_w=720)
Private room in Chatham
Front Deluxe Efficiency Studio
![](https://a0.muscache.com/im/pictures/miso/Hosting-695505433363661554/original/b9f637f5-f23d-4e38-af89-b9ca5a8db4ad.jpeg?im_w=720)
Private room in Fairhaven
Modern Deluxe Studio with Waterfront Views
Resort rentals with a gym
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NDA3MjQ2OTk%3D/original/bfd6dc9d-8dc6-4919-8ddd-627e1a435c2f.jpeg?im_w=720)
Private room in Hancock
4.78 out of 5 average rating, 32 reviewsMountainside 2 Bedroom at Jiminy Peak- No fees!
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-40724748/original/bb01367b-8f1c-479b-b797-130574495064.jpeg?im_w=720)
Private room in Hancock
4.66 out of 5 average rating, 80 reviewsCountry Village 3 Bedroom at Jiminy Peak- No fees!
![](https://a0.muscache.com/im/pictures/miso/Hosting-664439342171607721/original/e08bd22a-7d5f-4de9-85b6-b702f6979e65.jpeg?im_w=720)
Private room in Hancock
Large 1 Bedroom- Vacation Village in Berkshires
![](https://a0.muscache.com/im/pictures/f633d967-033c-425e-ac93-45a5a57b6201.jpg?im_w=720)
Private room in Hancock
Club Wyndham Bentley Brook - One Bedroom Suite
Destinations to explore
- Resort rentals United States
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