
Holiday rentals with a pool in Pioneer Valley
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pioneer Valley
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Pioneer Valley rentals with a pool
House rentals with a pool
Guest favourite

Home in Otis
4.92 out of 5 average rating, 13 reviewsBerkshires Oasis Retreat: Art Meets Nature
Top guest favourite

Home in Westhampton
5 out of 5 average rating, 29 reviewsHappy Valley getaway
Top guest favourite

Home in Great Barrington
4.99 out of 5 average rating, 74 reviewsStunning luxury home with pool
Guest favourite

Home in Brimfield
4.88 out of 5 average rating, 74 reviewsLuxury Home * Pool * Fireplace
Top guest favourite

Home in Chesterfield
4.98 out of 5 average rating, 60 reviewsHigh Field Farm
Top guest favourite

Home in Lanesborough
5 out of 5 average rating, 23 reviewsMountain Blossom Retreat by Evergreen Home
Guest favourite

Home in Cheshire
4.93 out of 5 average rating, 76 reviewsBerkshire County modern home + pool
Guest favourite

Home in Sheffield
4.96 out of 5 average rating, 27 reviewsPeaceful and Private Setting
Apartment rentals with a pool
Guest favourite

Apartment in Hancock
4.95 out of 5 average rating, 59 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Superhost

Apartment in New Ashford
5 out of 5 average rating, 5 reviewsWyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Apartment in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak

Apartment in Hancock
4.61 out of 5 average rating, 150 reviewsJiminy Peak Country Inn 1 Bedroom Suite
Superhost

Apartment in Hancock
5 out of 5 average rating, 4 reviewsWyndham Bentley Brook
Guest favourite

Apartment in Hancock
4.91 out of 5 average rating, 68 reviewsJiminy Peak Country Inn - ski in/out condo MT view

Apartment in Hancock
4.9 out of 5 average rating, 10 reviewsSki-in/Ski-Out on Jiminy Peak
Superhost

Apartment in Hancock
New place to stay2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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- Six Flags New England
- Monadnock State Park
- TPC River Highlands
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Brownstone Adventure Sports Park
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
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- Catamount Mountain Ski Resort
- Dinosaur State Park
- Mount Snow Ski Resort
- The Shattuck Golf Club
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- Beartown State Forest
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- Wintonbury Hills Golf Course
- Talcott Mountain State Park
- Hartford Golf Club
- Mount Sugarloaf State Reservation
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