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.
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
Home in Litchfield
4.93 out of 5 average rating, 162 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Home in Wilmington
4.9 out of 5 average rating, 130 reviews4 bedroom Ski House 15 min to Mount Snow
Jun 3 – 10
Home in Woodstock
4.93 out of 5 average rating, 207 reviewsCedar Ridge
Mar 24 – 31
Home in Keene
4.93 out of 5 average rating, 182 reviewsThe Brick House on Washington Street
Mar 13 – 20
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
Oct 2 – 9
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Feb 10 – 17
Home in Chesterfield
4.98 out of 5 average rating, 43 reviewsHigh Field Farm
Dec 4 – 11
Home in Shelburne Falls
4.95 out of 5 average rating, 19 reviewsBeautiful home for a cozy family getaway! W/pool !
Aug 5 – 12
Condo rentals with a pool
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun 4
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 7 – 14
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Mountain Oasis: Base of Mount Snow Retreat*
Sep 22 – 29
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
Oct 12 – 19
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Sep 29 – Oct 6
Condo in Dover
4.94 out of 5 average rating, 53 reviewsMt. Snow Dream Mtn View+Fireplace!
Sep 5 – 12
Condo in Dover
5.0 out of 5 average rating, 36 reviewsFour Seasons Slope-side Getaway at Mount Snow
May 29 – Jun 5
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 15 – 22
Destinations to explore
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