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Vacation rentals with a pool in Hillsborough County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hillsborough County
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 Hillsborough County rentals with a pool
House rentals with a pool
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Home in Henniker
New place to stayThe Pegasus Bungalow
![](https://a0.muscache.com/im/pictures/miso/Hosting-1067414685593917545/original/8785e0d9-ad3f-481a-a7d0-f68773c2255a.jpeg?im_w=720)
Superhost
Home in Winchendon
The Perfect Spot at the Lake @ Tatum's Place
![](https://a0.muscache.com/im/pictures/e2d30268-5362-428d-abe7-9976ec91c498.jpg?im_w=720)
Guest favourite
Home in Derry
4.83 out of 5 average rating, 126 reviewsBeautiful Lakefront Vacation
![](https://a0.muscache.com/im/pictures/miso/Hosting-856041410961923523/original/d54d569b-56f9-4c42-887b-c5dabc297ab0.jpeg?im_w=720)
Guest favourite
Home in Derry
4.88 out of 5 average rating, 104 reviewsSanctum by the Lake
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1067414685593917545/original/24a39b2c-46c8-40e4-8f32-04caae4b0541.jpeg?im_w=720)
Superhost
Home in Winchendon
5 out of 5 average rating, 3 reviewsAmazing Lakefront Home with Pool- Tatum's Place
![](https://a0.muscache.com/im/pictures/miso/Hosting-672496533837227657/original/fc3c0604-1792-47f5-8a82-9fd21131690e.jpeg?im_w=720)
Home in Litchfield
4.8 out of 5 average rating, 15 reviewsCheerful two bedroom home with pool, Dog Friendly
![](https://a0.muscache.com/im/pictures/miso/Hosting-600607210974080618/original/218b2d33-bdbd-4eb8-b63f-3481d7ab800d.jpeg?im_w=720)
Home in Bedford
4.63 out of 5 average rating, 30 reviewsBedford Retreat: pool, fenced yard.
![](https://a0.muscache.com/im/pictures/miso/Hosting-1168005159729758472/original/6c9cded4-c1ea-4732-976b-0c898dec0956.jpeg?im_w=720)
Home in Rindge
5 out of 5 average rating, 4 reviewsThe Shoreline
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