
Holiday houses in Hampshire County
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Top-rated holiday rentals in Hampshire County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Hampshire County holiday rentals
Other great holiday rentals in Hampshire County
Top Guest favourite

Apartment in Amherst
5 out of 5 average rating, 39 reviewsThe View Guest Suite - Amherst
Top Guest favourite

Apartment in Northampton
4.97 out of 5 average rating, 74 reviewsShort walk to town, 1894 house.
Guest favourite

Home in Belchertown
4.98 out of 5 average rating, 85 reviewsMoonstone Lake House – romantic, serene, fun!
Top Guest favourite

Loft in Amherst
5 out of 5 average rating, 19 reviewsSunny Studio Apartment
Superhost

Home in Deerfield
5 out of 5 average rating, 4 reviewsSerene South Deerfield Retreat
Top Guest favourite

Home in Sunderland
5 out of 5 average rating, 41 reviewsSunderland house - 5 College area
Top Guest favourite

Farm stay in Whately
5 out of 5 average rating, 26 reviewsBeautiful 18th Century Farmhouse
Top Guest favourite

Apartment in Northampton
4.99 out of 5 average rating, 69 reviewsNorthampton - 3rd-Floor - .5 mi to Smith/Downtown
Destinations to explore
- Rentals with a kayak Hampshire County
- Rentals with a patio Hampshire County
- Rentals with pools Hampshire County
- House rentals Hampshire County
- Rentals with a hot tub Hampshire County
- Rentals with lake access Hampshire County
- Apartment rentals Hampshire County
- Rentals with a fireplace Hampshire County
- Pet-friendly rentals Hampshire County
- Rentals with a fire pit Hampshire County
- Rentals with an EV charger Hampshire County
- Rentals with a washing machine and dryer Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Smoking-friendly rentals Hampshire County
- Rentals with outdoor seating Hampshire County
- Private suite rentals Hampshire County
- Six Flags New England
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- TPC River Highlands
- Bash Bish Falls State Park
- Bushnell Park
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Wintonbury Hills Golf Course
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Taconic State Park
- Dinosaur State Park
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Berkshire Botanical Garden
- Mount Snow Ski Resort