House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Great Barrington house rentals
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
Dec. 4 – 11
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
Dec. 5 – 12
Home in New Paltz
4.98 out of 5 average rating, 435 reviewsmidcentury modern in ground pool walk 2 trail/town
Nov. 26 – Dec. 3
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep. 13 – 20
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct. 27 – Nov. 3
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jul. 8 – 15
Home in Woodstock
4.91 out of 5 average rating, 209 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Sep. 20 – 27
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep. 8 – 15
Weekly house rentals
Home in Great Barrington
4.93 out of 5 average rating, 107 reviewsFormer Sunset View Inn
Jan. 19 – 26
Home in Canaan
5.0 out of 5 average rating, 134 reviewsCountry Cottage
Apr. 12 – 19
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
Oct. 2 – 9
Home in Woodstock
4.91 out of 5 average rating, 640 reviewsDutch Touch Woodstock Cottage
Nov. 19 – 26
Home in Great Barrington
4.96 out of 5 average rating, 113 reviewsModern Victorian on the Hill
Jan. 3 – 10
Home in Lee
4.9 out of 5 average rating, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep. 2 – 9
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
Jul. 17 – 24
Home in Egremont
4.9 out of 5 average rating, 109 reviewsCozy Berkshire Cape
Dec. 15 – 22
Private house rentals
Home in Great Barrington
5.0 out of 5 average rating, 8 reviewsCharming Cottage - Walk To Town
May 1 – 8
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
Dec. 16 – 23
Home in Stockbridge
4.94 out of 5 average rating, 90 reviewsBright Stockbridge country home, near everything!
Dec. 10 – 17
Home in Great Barrington
4.87 out of 5 average rating, 47 reviewsCountryside Calm. Proximity to Berkshires' Best!
May 28 – Jun. 4
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
Sep. 1 – 8
Home in Great Barrington
5.0 out of 5 average rating, 3 reviewsWalt's Townhouse - Berkshire living at its best
Sep. 29 – Oct. 6
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
Nov. 27 – Dec. 4
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsRenovated Downtown Great Barrington House
May 27 – Jun. 3
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 CAD before taxes and fees
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