Hampshire County rentals with pool

We found 43 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

October 2025

November 2025

Explore Hampshire County rentals with pools

Premier Host

The Clearing - Quiet - Close To Nature

Sleeps 4 · 1 bedroom · 1 bathroom

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Sleeps 14 · 5 bedrooms · 3 bathrooms

Located on 7 acres of property far enough for retreat, but close enough to town.

Premier Host

Sun filled pool house with vaulted ceilings beautiful in ground pool and gardens

Sleeps 4 · 1 bedroom

Find spaces that suit your style

House

Condo/Apartment

Rentals with Pool in Hampshire County

Rentals with Pool in Plainfield

Rentals with Pool in Middlefield

Rentals with Pool in Hatfield

Rentals with Pool in Florence

Rentals with Pool in Goshen

Rentals with Pool in Belchertown

Rentals with Pool in Southampton

Rentals with Pool in Amherst

Rentals with Pool in Hadley

Rentals with Pool in Cummington

Rentals with Pool in Huntington

Rentals with Pool in Granby

Rentals with Pool in Worthington

Rentals with Pool in Chesterfield

Rentals with Pool in Easthampton

Rentals with Pool in Northampton

Rentals with Pool in Westhampton

Rentals with Pool in Ware

Rentals with Pool in Williamsburg

Holiday Rental options in Hampshire County

Ski holiday rentals in Hampshire County

Holiday rentals with spa pool in Hampshire County

Beach holiday rentals in Hampshire County

Lake holiday rentals in Hampshire County

Mountain holiday rentals in Hampshire County

Oceanfront holiday rentals in Hampshire County

Family-friendly holiday rentals in Hampshire County

Pet-friendly holiday rentals in Hampshire County

It's easy to contact hosts and keep track of all your messages when you have a Bookabach account