Cottage holiday rentals in The Berkshires
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Top-rated cottage rentals in The Berkshires
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in The Berkshires
Cottage rentals with a hot tub
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
20–27 Feb
Cottage in Red Hook
4.92 out of 5 average rating, 324 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
27 Apr – 4 May
Cottage in Woodstock
4.9 out of 5 average rating, 376 reviewsFamous Architect - Streamside Cottage w/ hot tub
14–21 Sep
Cottage in Phoenicia
4.89 out of 5 average rating, 804 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
27 Sep – 4 Oct
Cottage in Kent
4.88 out of 5 average rating, 153 reviewsNEW - Hot Tub - Mohawk Mtn - Appalachian Trl
31 Dec – 7 Jan
Cottage in Guilford
4.96 out of 5 average rating, 159 reviewsLuxury cottage by the sea with hot tub and pool
22–29 Apr
Cottage in Denver
4.96 out of 5 average rating, 110 reviewsCountry Cottage w/ HOT TUB & Views
24 Jun – 1 Jul
Cottage in Kerhonkson
4.85 out of 5 average rating, 142 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
24–31 Dec
Pet-friendly cottage rentals
Cottage in Florida
4.82 out of 5 average rating, 102 reviewsPeaceful Mountain Cabin by Ski, Kayak, Museums +!
7–14 Apr
Cottage in Granby
4.87 out of 5 average rating, 138 reviewsThe Little Red Schoolhouse ~ Circa 1877
3–10 Apr
Cottage in Catskill
4.96 out of 5 average rating, 233 reviews1930's Cottage charm air conditioned near hiking
6–13 Nov
Cottage in Sharon
4.9 out of 5 average rating, 125 reviewsFoxfire Hill: A Bit of Luxury in the Countryside
2–9 Oct
Cottage in Gilboa
4.94 out of 5 average rating, 201 reviewsHome Alone Mountain Retreat
16–23 Sep
Cottage in Orange
4.95 out of 5 average rating, 199 reviewsThe Fishing Cottage: A Sweetwater Stay
19–26 Jan
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
13–20 Jul
Cottage in Sheffield, The Berkshires
4.93 out of 5 average rating, 105 reviewsCheerful 3-bedroom cottage with woodstove.
17–24 Jan
Private cottage rentals
Cottage in Chichester
4.99 out of 5 average rating, 514 reviewsGarden Cottage In The Catskills
17–24 Aug
Cottage in Valatie
4.99 out of 5 average rating, 127 reviewsKinderhook Lake Retreat-private+kayaks/sup+swim+ac
8–15 Sep
Cottage in Saugerties
4.93 out of 5 average rating, 218 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
6–13 Oct
Cottage in Collinsville
4.96 out of 5 average rating, 113 reviewsThe Carriage House
27 Sep – 4 Oct
Cottage in Kerhonkson
4.94 out of 5 average rating, 257 reviewsBlue Haven in the Catskills
12–19 Sep
Cottage in Woodstock
4.99 out of 5 average rating, 278 reviewsGrapevine Cottage
15–22 Apr
Cottage in Roxbury
4.98 out of 5 average rating, 482 reviewsThe Little House
19–26 Feb
Cottage in Rhinebeck
4.99 out of 5 average rating, 121 reviewsFabulous Lemon Cottage in Rhinebeck, NY
15–22 Jul
Destinations to explore
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