House holiday rentals in Great Barrington
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Top-rated house rentals in Great Barrington
Guests agree: these houses 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 house rentals in Great Barrington
House rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
12–19 Nov
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
30 Dec – 6 Jan
Home in New Paltz
4.98 out of 5 average rating, 435 reviewsmidcentury modern in ground pool walk 2 trail/town
26 Nov – 3 Dec
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
22–29 Nov
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
16–23 May
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
23–30 Jun
Home in Woodstock
4.91 out of 5 average rating, 209 reviewsJapanese Teahouse & Onsen, outside shower, tennis
20–27 Sep
Weekly house rentals
Home in Canaan
5.0 out of 5 average rating, 134 reviewsCountry Cottage
16–23 Mar
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
5–12 Jun
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
5–12 Jun
Home in Great Barrington
4.93 out of 5 average rating, 107 reviewsFormer Sunset View Inn
15–22 Jan
Home in Woodstock
4.91 out of 5 average rating, 640 reviewsDutch Touch Woodstock Cottage
22–29 Mar
Home in Great Barrington
4.96 out of 5 average rating, 113 reviewsModern Victorian on the Hill
2–9 Jun
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
2–9 Oct
Home in Lee
4.9 out of 5 average rating, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
2–9 Sep
Private house rentals
Home in Great Barrington
5.0 out of 5 average rating, 3 reviewsWalt's Townhouse - Berkshire living at its best
28 May – 4 Jun
Home in Great Barrington
5.0 out of 5 average rating, 8 reviewsCharming Cottage - Walk To Town
3–10 May
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
16–23 Dec
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
9–16 Sep
Home in Stockbridge
4.94 out of 5 average rating, 90 reviewsBright Stockbridge country home, near everything!
9–16 Nov
Home in Great Barrington
4.87 out of 5 average rating, 47 reviewsCountryside Calm. Proximity to Berkshires' Best!
4–11 May
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
4–11 Jan
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
18–25 Dec
Quick stats about house rentals in Great Barrington
Total rentals
150 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
4K reviews
Nightly prices starting at
$68 SGD before taxes and fees
Destinations to explore
- New City Holiday rentals
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