
Family-friendly holiday rentals in Hampshire County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Hampshire County
Guests agree: These family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub

The View Guest Suite - Amherst

Sweet suite, walk to town tout suite!

The Creation Station

Serene South Deerfield Retreat

Hilltown Cabin Hideaway: A River Runs Through It!

The Farmhouse - Hot tub eclectic farmhouse 3 br

Luxury Glamping, Private, Wood Burning Hot Tub

Clean and sunny house near Smith College
Family- and pet-friendly home rentals

Entire 1-st Floor Apt & Specials for 3+ Stays

Light filled three bedroom apartment DT Florence!

Berkshires Cottage by Lake. Year Round Adventures.

Bright Noho studio suite perfect walk to downtown

Peaceful Cabin in the Woods

Cedar Wet Room w Soaking Tub

Zachariah House Main St. Ashfield

House Above the Hollow
Family-friendly home rentals with a pool

Stay in Robert Frost's beautiful house

Sunset Ridge

Happy Valley getaway

Nestled Inn

Sweet cape near U Mass

NE Historical Mansion-pets and pet lovers welcome

High Field Farm

Enjoy every season the Berkshires have to offer.
Destinations to explore
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Rentals with an EV charger Hampshire County
- Rentals with a patio Hampshire County
- Rentals with a washing machine and dryer Hampshire County
- Apartment rentals Hampshire County
- Pet-friendly rentals Hampshire County
- Rentals with a fireplace Hampshire County
- Rentals with a kayak Hampshire County
- Rentals with lake access Hampshire County
- House rentals Hampshire County
- Rentals with a hot tub Hampshire County
- Rentals with a fire pit Hampshire County
- Rentals with pools Hampshire County
- Private suite rentals Hampshire County
- Smoking-friendly rentals Hampshire County
- Rentals with outdoor seating Hampshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- TPC River Highlands
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Brimfield State Forest
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Bigelow Hollow State Park
- Taconic State Park
- Dinosaur State Park
- Mount Sugarloaf State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Mount Snow Ski Resort