
House holiday rentals in Hampshire County
Find and book unique houses on Airbnb
Top-rated house rentals in Hampshire County
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Hampshire County house rentals
House rentals with a pool

High Field Farm

Stay in Robert Frost's beautiful house

Happy Valley getaway

Morning Side

Sun-drenched 6BR Victorian steps from downtown

Calm Post+Beam Retreat

Perfectly Polished Deerfield Home 5 min to I-91
Weekly house rentals

J&J’s Retreat

Forest Home with Sauna

Low-scent, historic, well-located downtown house

Cute and Cozy Lake Cottage

Spacious Lake Front Home

Lakefront Cottage on Private Beach

Great/Ideal place near UMass for Graduation

Lakefront Jewel By: Evergreen Home
Private house rentals

Spacious and lovely house with hot tub

Sunny Valley Mountain View

Luxury log style home with views to Mt. Monadnock!

Home Away from Home in Northampton

Pristine Home In Becket Woods

An oasis - spacious and bright

Relax & Enjoy it all to yourself

Berkshires Lakefront Stylish Retreat w/Gameroom
Destinations to explore
- Rentals with pools Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Kid-friendly rentals Hampshire County
- Pet-friendly rentals Hampshire County
- Rentals with an EV charger Hampshire County
- Private suite rentals Hampshire County
- Rentals with outdoor seating Hampshire County
- Rentals with a fire pit Hampshire County
- Rentals with a fireplace Hampshire County
- Apartment rentals Hampshire County
- Smoking-friendly rentals Hampshire County
- Rentals with a hot tub Hampshire County
- Rentals with a kayak Hampshire County
- Rentals with a washing machine and dryer Hampshire County
- Rentals with a patio Hampshire County
- Rentals with lake access Hampshire County
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- Jiminy Peak Mountain Resort
- Six Flags New England
- Monadnock State Park
- Catamount Mountain Ski Resort
- TPC River Highlands
- Bash Bish Falls State Park
- Mount Snow Ski Resort
- Bushnell Park
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Rockledge Golf Club
- Bright Nights at Forest Park
- Brimfield State Forest
- Bigelow Hollow State Park
- The Shattuck Golf Club
- Hancock Shaker Village
- Pineridge Cross Country Ski Area
- Beartown State Forest
- Naumkeag