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Vacation 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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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pioneer Valley rentals with a pool
House rentals with a pool
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Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 168 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
![](https://a0.muscache.com/im/pictures/c1a0dac1-2134-4915-984e-1d595de18706.jpg?im_w=720)
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 152 reviewsAdams Farm-"The Little Farmhouse"
![](https://a0.muscache.com/im/pictures/6cd12422-2e27-48bf-9813-660f3745b832.jpg?im_w=720)
Guest favorite
Home in Keene
4.93 out of 5 average rating, 188 reviewsThe Brick House on Washington Street
![](https://a0.muscache.com/im/pictures/miso/Hosting-24440275/original/05ca6479-82f6-420a-8450-7493179e68b1.jpeg?im_w=720)
Guest favorite
Home in Woodstock
4.93 out of 5 average rating, 214 reviewsCedar Ridge
![](https://a0.muscache.com/im/pictures/miso/Hosting-23686706/original/821741e4-d448-4da0-ac63-35bc4b681dd4.jpeg?im_w=720)
Superhost
Home in Wilmington
4.9 out of 5 average rating, 133 reviews4 bedroom Ski House 15 min to Mount Snow
![](https://a0.muscache.com/im/pictures/miso/Hosting-50616692/original/8840debd-e168-49bb-b40b-304a19cfc665.jpeg?im_w=720)
Guest favorite
Home in Chesterfield
4.98 out of 5 average rating, 48 reviewsHigh Field Farm
![](https://a0.muscache.com/im/pictures/miso/Hosting-812353630139434779/original/48380701-bb4d-4333-a94a-913eab93131e.jpeg?im_w=720)
Guest favorite
Home in Amherst
5 out of 5 average rating, 29 reviewsCalm Post+Beam Retreat
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MTAwOTAxODc3OTA4NTk0OTY0MQ%3D%3D/original/ce32a022-8274-44d1-9a2f-2d011478c036.jpeg?im_w=720)
Guest favorite
Home in New Hartford
4.93 out of 5 average rating, 14 reviewsMountain Serenity Lake View Pool & Hot Tub
Condo rentals with a pool
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Guest favorite
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
![](https://a0.muscache.com/im/pictures/miso/Hosting-21277776/original/6354ed9d-2f8d-4f27-84b3-43f4730dd34f.jpeg?im_w=720)
Guest favorite
Condo in Hancock
4.83 out of 5 average rating, 132 reviewsCozy Condo @ Jiminy Peak
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MzY2MzkxOTA%3D/original/50cfedf2-3dab-4b00-81fa-93ef15c35ba1.jpeg?im_w=720)
Guest favorite
Condo in Dover
4.99 out of 5 average rating, 106 reviews*Summer Mountain Oasis: Base of Mount Snow
![](https://a0.muscache.com/im/pictures/cd7f4830-5e71-4e06-b118-d8533309e639.jpg?im_w=720)
Guest favorite
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
![](https://a0.muscache.com/im/pictures/1984be93-7be5-4080-b5b2-67c4d91a9f44.jpg?im_w=720)
Guest favorite
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
![](https://a0.muscache.com/im/pictures/d4462de0-2d4f-4fe5-90e5-113419e1b711.jpg?im_w=720)
Guest favorite
Condo in Dover
5 out of 5 average rating, 39 reviewsFour Seasons Slope-side Getaway at Mount Snow
![](https://a0.muscache.com/im/pictures/miso/Hosting-702211555543798142/original/3c38a56f-dd40-4322-a206-b2086c375a42.jpeg?im_w=720)
Guest favorite
Condo in Dover
4.96 out of 5 average rating, 24 reviewsSki in Ski out condo great location
![](https://a0.muscache.com/im/pictures/8c3505dd-644a-455a-8bfe-4c647b0499d2.jpg?im_w=720)
Guest favorite
Condo in Dover
4.89 out of 5 average rating, 87 reviews⛷ Walk to Mt. Snow-Spa-Pool-Fireplace ⛷
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