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Vacation rentals with a pool in Hampshire County

Find and book unique homes with a pool on Airbnb

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Top-rated rentals with a pool in Hampshire County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Bungalow in Easthampton
The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John
May 6 – 13
$131 per night
Apartment in Northampton
Luxury w sunny balcony in best downtown location
Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.
May 28 – Jun 4
$181 per night
Guest favorite
Home in Amherst
Calm Post+Beam Retreat
Escape into our airy, light-filled, modern, cabin. Built with wood milled right here, this serene retreat has lovely sunset views. 700 sqf detached cabin. Sleeping + office loft, 2nd queen sleeper, wood-burning stove, digital thermostat, wifi, 55” TV with Netflix, ample parking. Summer dips in the pool. North Amherst is 10 min from Amherst center, UMASS, Amherst College; 27 min to Smith College. **To access the 2nd floor office, you need to step over a beam. 1-step to the front door.
Apr 13 – 20
$143 per night

Popular amenities for Hampshire County rentals with a pool

House rentals with a pool

Guest favorite
Home in Chesterfield
High Field Farm
Dec 19 – 26
$451 per night
Guest favorite
Home in Amherst
Stay in Robert Frost's beautiful house
Jun 23 – 30
$506 per night
Home in Granby
Serene Rustic Hideaway w/ Pool in Granby!
Aug 22 – 29
$363 per night
Home in Chicopee
A large private space.
Jan 25 – Feb 1
$120 per night
Home in Williamsburg
Valley View Farms Home Pool Hot Tub EV Charger
Jan 23 – 30
$899 per night
Home in Worthington
Morning Side
Jul 23 – 30
$546 per night

Destinations to explore