
Holiday rentals with a pool in Hampshire County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hampshire County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Hampshire County rentals with a pool
House rentals with a pool
Top guest favourite

Home in Chesterfield
4.98 out of 5 average rating, 58 reviewsHigh Field Farm
CatherineRating, 5 stars1 week ago
Such a relaxing place, space for everyone to spread out and to gather…kids played in the barn because it was a rainy weekend and sadly too cold for a swim. Great kitchen with all necessities. four minutes to gorge trail head where my son ran 50 miles in the beast coast ultra. highly recommend

Home in Amherst
5 out of 5 average rating, 8 reviewsStay in Robert Frost's beautiful house
HilaryRating, 5 stars20 months ago
Lovely home. Everything was as great as we expected. Alexander is a superb host. There was even a great book collection! We look forward to coming back. Thank you Alexander!
Top guest favourite

Home in Westhampton
5 out of 5 average rating, 26 reviewsHappy Valley getaway
DamarisRating, 5 stars3 days ago
We enjoyed our stay! Everything was beautiful and our Hosts were great and very responsive. We would definitely recommend and hopefully get to come back again!
Guest favourite

Home in Worthington
5 out of 5 average rating, 7 reviewsMorning Side
RebeccaRating, 5 stars6 months ago
Morning Side is filled with character and charm. The house itself, the furnishings, and even the book collection take you back to 18th century New England. The kitchen and dining area are particularly cozy and inviting. The windows and views are magical, particularly with a good snowfall. The host was very helpful, particularly proactive about preparing the sidewalk and driveway for snowfall, even on Thanksgiving Day!
Guest favourite

Home in Northampton
5 out of 5 average rating, 14 reviewsSun-drenched 6BR Victorian steps from downtown
KevinRating, 5 stars2 weeks ago
I wish I had known about this property sooner for my visits to Amherst College. It was better than advertised. Sunny, clean, comfortable and so close to walk to town. My whole family enjoyed it very much.

Home in Deerfield
4.81 out of 5 average rating, 226 reviewsPerfectly Polished Deerfield Home 5 min to I-91
WillRating, 5 stars2 weeks ago
good space for a medium sized group or family. hosta are very nice. beautiful surroundings.
Guest favourite

Home in South Hadley
5 out of 5 average rating, 6 reviewsDog friendly, 2 fireplaces,Pool, Pickleball, 3 bd
BrianRating, 5 stars8 months ago
This was exactly what we needed for a trip out to see our son at school. Not only did it have what we needed but so much we didn't know we wanted. An excellent kitchen, plenty of space, dog friendly, a pool and pickleball! We had a couple of big battles with the kids while they were at the house for some much needed home cooking. The bed was very comfortable and Mary was very helpful if needed. I look forward to many future stays at Mary's home
Destinations to explore
- Rentals with a firepit Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Pet-friendly rentals Hampshire County
- Rentals with a washing machine and dryer Hampshire County
- Rentals with an EV charger Hampshire County
- Rentals with a hot tub Hampshire County
- House rentals Hampshire County
- Smoking-friendly rentals Hampshire County
- Private suite rentals Hampshire County
- Flat rentals Hampshire County
- Rentals with a fireplace Hampshire County
- Family-friendly rentals Hampshire County
- Rentals with a patio Hampshire County
- Rentals with a kayak Hampshire County
- Rentals with outdoor seating Hampshire County
- Rentals with lake access Hampshire County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Six Flags New England
- Monadnock State Park
- TPC River Highlands
- Jiminy Peak Mountain Resort
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Dinosaur State Park
- Brimfield State Forest
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Naumkeag
- Brignole Vineyards
- The Shattuck Golf Club