
Family-friendly vacation 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.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Belchertown Apartment - near UMass & 5 colleges
1 bedroom, 1 bath apartment w full kitchen in Belchertown. Private bedroom sleeps 2. Futon in living area can sleep a 3rd. Perfect location if interested in exploring Western MA or looking for a spot to stay when visiting someone attending one of the local five colleges. 20 min to Northampton, 10 min to downtown Amherst, 15 min to UMass, 7 min to the popular wedding venue The Red Barn at Hampshire College.Within 30 min of Yankee Candle, amazing hiking, Mike's Maze, & apple picking.35 min to MGM

Serene 1-br suite on 75 acre horse property
Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

Separate apt, 1 mile from downtown, 1 guest only
This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. Weโre located in Village Hill.

Cozy Hilltown Cottage
Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Happy Maples!
I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

Hadley Hay House | No Cleaning fees!
Rest easy in this picturesque, very spacious tranquil home ready for you for a relaxing stay. Minutes from umass, 10min to either Amherst or Noho. Not only will you have access to the hot tub and walk in the hay fields behind the house but we are directly across from the Connecticut River. Perfect spot for swimming or kayaking. Enjoy a beautiful view of the mountains/hay and corn fields from multiple rooms in the house. This space is above an all female wood working shop, happy to give tour!

Bright private suite mins. from Five College area
Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Cafรฉ. Suite is professionally cleaned between each stay.

The Floating Library: private hiker's hideaway
Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming, above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and lots of magical touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

Mountain Retreat close to Northampton & Amherst!
Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Tiny House Farm Retreat: Mountain Views, Fire pit
The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.
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!

Mossy Glen Glampsite and Hot Tubs

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

Long Mountain Suite W/Hot tub
Family- and pet-friendly home rentals

Light filled three bedroom apartment DT Florence!

Peaceful Cabin in the Woods

Berkshires Cottage by Lake. Year Round Adventures.

Mill River Cottage (pet friendly!)

Zachariah House Main St. Ashfield

The cozy clubhouse

Private Guest House Downtown Noho

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

Light-bathed comfort, wood + charm, right downtown

Sunset Ridge

Happy Valley getaway

Sweet cape near U Mass

NE Historical Mansion-pets and pet lovers welcome

Enjoy every season the Berkshires have to offer.

Morning Side

1880s balconied luxury pad, best downtown location
Destinations to explore
- Rentals with poolsย Hampshire County
- House rentalsย Hampshire County
- Rentals with an EV chargerย Hampshire County
- Bed and breakfastsย Hampshire County
- Rentals with breakfastย Hampshire County
- Apartment rentalsย Hampshire County
- Private suite rentalsย Hampshire County
- Smoking-friendly rentalsย Hampshire County
- Rentals with beach accessย Hampshire County
- Rentals with lake accessย Hampshire County
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- Guesthouse rentalsย Hampshire County
- Rentals with a fire pitย Hampshire County
- Rentals with a patioย Hampshire County
- Rentals with a hot tubย Hampshire County
- Pet-friendly rentalsย Hampshire County
- Rentals with a kayakย Hampshire County
- Rentals with a washer and dryerย Hampshire County
- Family-friendly rentalsย Massachusetts
- Family-friendly rentalsย United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Mount Snow Ski Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- University of Connecticut
- Dcu Center
- Ski Sundown
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Smith College
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- Hancock Shaker Village
- Connecticut Convention Center
- Mount Holyoke College





