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
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
Guest favorite
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Guest favorite
Home in Keene
4.93 out of 5 average rating, 184 reviewsThe Brick House on Washington Street
Guest favorite
Home in Woodstock
4.93 out of 5 average rating, 210 reviewsCedar Ridge
Guest favorite
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Guest favorite
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Superhost
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Condo rentals with a pool
Guest favorite
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Guest favorite
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Guest favorite
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Guest favorite
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
Guest favorite
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Guest favorite
Condo in Dover
4.96 out of 5 average rating, 23 reviewsSki in Ski out condo great location
Superhost
Condo in Dover
4.77 out of 5 average rating, 91 reviewsCozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Guest favorite
Condo in Dover
5.0 out of 5 average rating, 36 reviewsFour Seasons Slope-side Getaway at Mount Snow
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