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Vacation rentals with a pool in Berkshire County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Berkshire County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Berkshire County rentals with a pool
House rentals with a pool
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Home in New Lebanon
4.98 out of 5 average rating, 50 reviewsBerkshire Mountain retreat gorgeous views and pool
![](https://a0.muscache.com/im/pictures/c5c24878-11f8-4cc3-baa3-cc455ad4593a.jpg?im_w=720)
Home in West Stockbridge
5 out of 5 average rating, 19 reviewsBerkshire House on the Hill
![](https://a0.muscache.com/im/pictures/hosting/Hosting-654237794577824151/original/a7dd5f20-2b5e-47f1-9591-f211b30ab275.jpeg?im_w=720)
Home in Pittsfield
5 out of 5 average rating, 45 reviewsPalatial, central Berkshire, large family home
![](https://a0.muscache.com/im/pictures/miso/Hosting-43107290/original/3bdd9c9d-16d2-4aae-876e-96f99bb74c1b.jpeg?im_w=720)
Home in Pittsfield
4.98 out of 5 average rating, 42 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1101548942340690894/original/7e54d1b0-8ae3-400e-bbc6-54dcb0a789ca.jpeg?im_w=720)
Home in Egremont
5 out of 5 average rating, 4 reviewsCatamount House w. Pool/Hot Tub
![](https://a0.muscache.com/im/pictures/miso/Hosting-51753218/original/ddd096ce-5d22-4317-8008-f0eddd012da3.jpeg?im_w=720)
Home in Great Barrington
5 out of 5 average rating, 36 reviewsSix-bedroom country house with pool and hot tub
![](https://a0.muscache.com/im/pictures/miso/Hosting-878316406625449785/original/2e6aab55-a054-42c5-871f-da78cd626757.jpeg?im_w=720)
Home in New Marlborough
4.96 out of 5 average rating, 23 reviewsBerkshires Colonial Farmhouse
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-741687595946105153/original/56e6590d-af99-49d5-83e6-01bbf79ce30f.jpeg?im_w=720)
Home in Hillsdale
4.9 out of 5 average rating, 20 reviewsPanoramic Hilltop Views w/ Pool near Catamount
Condo rentals with a pool
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Condo in Hancock
4.95 out of 5 average rating, 21 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
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Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
![](https://a0.muscache.com/im/pictures/6eaa2b97-d15a-4bdb-918e-db186c170877.jpg?im_w=720)
Condo in Hancock
4.92 out of 5 average rating, 24 reviewsJiminy Peak Apartment
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Condo in Hancock
4.9 out of 5 average rating, 52 reviewsJiminy Peak Country Inn - ski in/out condo MT view
![](https://a0.muscache.com/im/pictures/5513ea0d-d0c1-4995-9f66-08b57ec257e8.jpg?im_w=720)
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
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Condo in Hancock
4.97 out of 5 average rating, 37 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
![](https://a0.muscache.com/im/pictures/29e53d0e-9b0d-438a-bd47-a1e017f54989.jpg?im_w=720)
Condo in Hancock
4.97 out of 5 average rating, 30 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-1034976259642871564/original/600ac0d8-f7d8-44c2-8ef2-03aaa0fa5962.jpeg?im_w=720)
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
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