House holiday rentals in Stockbridge
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Top-rated house rentals in Stockbridge
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 Stockbridge house rentals
House rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
22 – 29 Mar
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
6 – 13 Sept
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13 – 20 Sept
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
14 – 21 July
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
6 – 13 Nov
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
10 – 17 Sept
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
23 – 30 Aug
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12 – 19 Sept
Weekly house rentals
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
2 – 9 Apr
Home in Egremont
4.97 out of 5 average rating, 112 reviewsA sunny, quiet chalet beautifully decorated.
16 – 23 Apr
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
9 – 16 Jan
Home in Catskill
4.96 out of 5 average rating, 136 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
21 – 28 Sept
Home in Becket
4.95 out of 5 average rating, 37 reviewsNerd Preservation Sanctuary
10 – 17 Dec
Home in Stockbridge
4.95 out of 5 average rating, 91 reviewsBright Stockbridge country home, near everything!
23 – 30 Dec
Home in Lee
5.0 out of 5 average rating, 36 reviewsGreenHouse
15 – 22 Oct
Home in Stockbridge
4.98 out of 5 average rating, 85 reviewsGreek Revival Farmhouse
16 – 23 Mar
Private house rentals
Home in Great Barrington
5.0 out of 5 average rating, 68 reviewsGranite Ledge, Modern home in a unique setting
30 Oct – 6 Nov
Home in Lee
5.0 out of 5 average rating, 11 reviewsBerkshires Manor for Lasting Memories
27 Sept – 4 Oct
Home in West Stockbridge
4.98 out of 5 average rating, 57 reviewsBerkshires-Enjoy The Peak, private home
23 – 30 Sept
Home in West Stockbridge
4.97 out of 5 average rating, 59 reviewsPanoramic Views, Indoor Pool by Evergreen Home
15 – 22 Nov
Home in Great Barrington
4.93 out of 5 average rating, 68 reviewsQuiet home on the hill.
8 – 15 Nov
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
24 – 31 Oct
Home in Great Barrington
5.0 out of 5 average rating, 34 reviewsThe Yellow Victorian With Chefs Kitchen
3 – 10 Dec
Home in Chatham
4.98 out of 5 average rating, 97 reviewsHilltop studio apartment on 100 acres near village
24 – 31 May
Quick stats about house rentals in Stockbridge
Total rentals
60 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
2.3K reviews
Nightly prices starting at
$151 AUD before taxes and fees
Destinations to explore
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