Resort holiday rentals in Massachusetts
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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
Hotel room in Brewster
4.46 out of 5 average rating, 56 reviewsOcean Edge Resort One Bedroom Villa
9–16 Jan
Resort in Brewster
4.35 out of 5 average rating, 81 reviewsOcean Edge Resort One Bedroom Villa
24–31 Jan
Resort in Dennis
4.75 out of 5 average rating, 4 reviewsBeachfront 1 BR Suite, Dennis Port July 12 - 19
7–14 Aug
Resort in Brewster
4.52 out of 5 average rating, 46 reviewsOcean Edge Resort One Bedroom Condo
15–22 Sep
Resort in Dennis
4.6 out of 5 average rating, 5 reviewsOcean front 2-bedroom suite on beautiful beach
18–25 Dec
Resort rentals with a pool
Resort in Dennis
4.67 out of 5 average rating, 3 reviewsBeachside Cape Cod Resort
22–29 Jun
Resort in Dennis
4.75 out of 5 average rating, 4 reviewsBeachfront 1 BR Suite, Dennis Port July 12 - 19
7–14 Aug
Resort in Hancock
4.66 out of 5 average rating, 180 reviewsCountry Inn Suite at Jiminy Peak - No fees added
1–8 Jun
Hotel room in Wellfleet
4.87 out of 5 average rating, 38 reviewsThe Motel at Even'tide Resort - One Queen Bed
13–20 Sep
Hotel room in Wellfleet
4.82 out of 5 average rating, 11 reviewsThe Motel at Even'tide Resort - One Bedroom Suite
19–26 May
Resort in Hancock
4.62 out of 5 average rating, 68 reviewsCountry Village 3 Bedroom at Jiminy Peak- No fees!
15–22 Jul
Resort in Hancock
4.76 out of 5 average rating, 29 reviewsMountainside 2 Bedroom at Jiminy Peak- No fees!
14–21 Oct
Hotel room in Wellfleet
4.63 out of 5 average rating, 27 reviewsThe Motel at Even'tide Resort - One King Bed
9–16 Jun
Resort rentals with a gym
Hotel room in Wellfleet
4.82 out of 5 average rating, 11 reviewsThe Motel at Even'tide Resort - One Bedroom Suite
19–26 May
Resort in Hancock
4.62 out of 5 average rating, 68 reviewsCountry Village 3 Bedroom at Jiminy Peak- No fees!
15–22 Jul
Hotel room in Wellfleet
4.63 out of 5 average rating, 27 reviewsThe Motel at Even'tide Resort - One King Bed
9–16 Jun
Resort in Hancock
4.76 out of 5 average rating, 29 reviewsMountainside 2 Bedroom at Jiminy Peak- No fees!
14–21 Oct
Hotel room in Wellfleet
The Motel at Even'tide Resort - Studio Efficiency
25 Aug – 1 Sep
Resort in Hancock
Club Wyndham Bentley Brook - One Bedroom Suite
4–11 Nov
Resort in Hancock
Large 1 Bedroom- Vacation Village in Berkshires
25 Aug – 1 Sep
Resort in Hancock
Club Wyndham Bentley Brook - Studio
14–21 May
Destinations to explore
- Resort rentals United States
- Bed and breakfasts Massachusetts
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