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
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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
4–11 Dec
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
5–12 Dec
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 Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sept
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
27 Oct – 3 Nov
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
8–15 Jul
Home in Woodstock
4.91 out of 5 average rating, 209 reviewsJapanese Teahouse & Onsen, outside shower, tennis
20–27 Sept
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
8–15 Sept
Weekly house rentals
Home in Great Barrington
4.93 out of 5 average rating, 107 reviewsFormer Sunset View Inn
19–26 Jan
Home in Canaan
5.0 out of 5 average rating, 134 reviewsCountry Cottage
12–19 Apr
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
2–9 Oct
Home in Woodstock
4.91 out of 5 average rating, 640 reviewsDutch Touch Woodstock Cottage
19–26 Nov
Home in Great Barrington
4.96 out of 5 average rating, 113 reviewsModern Victorian on the Hill
3–10 Jan
Home in Lee
4.9 out of 5 average rating, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
2–9 Sept
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
17–24 Jul
Home in Egremont
4.9 out of 5 average rating, 109 reviewsCozy Berkshire Cape
15–22 Dec
Private house rentals
Home in Great Barrington
5.0 out of 5 average rating, 8 reviewsCharming Cottage - Walk To Town
1–8 May
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
16–23 Dec
Home in Stockbridge
4.94 out of 5 average rating, 90 reviewsBright Stockbridge country home, near everything!
10–17 Dec
Home in Great Barrington
4.87 out of 5 average rating, 47 reviewsCountryside Calm. Proximity to Berkshires' Best!
28 May – 4 Jun
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
1–8 Sept
Home in Great Barrington
5.0 out of 5 average rating, 3 reviewsWalt's Townhouse - Berkshire living at its best
29 Sept – 6 Oct
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
27 Nov – 4 Dec
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsRenovated Downtown Great Barrington House
27 May – 3 Jun
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
£40 before taxes and fees
Destinations to explore
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