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.

Guest favorite
Guest suite in Northampton
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. We’re located in Village Hill.
Dec 28 – Jan 4
$89 per night
4.86 out of 5 average rating, 434 reviews
Guest favorite
Apartment in Pelham
Pelham 2nd floor Apartment
Second floor newly finished apartment that accommodates 2 guest. Well water and septic. Green by recycling and using salvage materials. Environmentally benign materials used where possible. Solar. Utilities and internet included. Raspberries and blueberries in season. 3.9 miles from UMASS and Amherst Colleges. 5.3 miles from Hampshire College. 11 miles from Mt. Holyoke and 12 miles from Smith College. NO PETS ACCEPTED! Allergy free. Don't hesitate to contact us with questions!
Mar 16 – 23
$80 per night
4.99 out of 5 average rating, 124 reviews
Guest favorite
Apartment in Amherst
Amherst, Quiet, Private, Spacious Studio apartment
This airy, bright studio apartment is a short drive to the University of Massachusetts, Hampshire College, Amherst College, and Mt. Holyoke College in South Hadley and Smith College in Northampton. We are in the Pioneer Valley, a treasure trove of amazing views, forests and waterways as well as gourmet dining and music venues. We are about 2 miles to the Eric Carle Museum, the Yiddish Book Center, Emily Dickinson Museum, art museums and galleries as well as hiking trails.
Nov 11 – 18
$104 per night
4.9 out of 5 average rating, 222 reviews

Popular amenities for Hampshire County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Northampton
The Farmhouse - Hot tub eclectic farmhouse 3 br
Jun 16 – 23
$256 per night
4.88 out of 5 average rating, 554 reviews
Guest favorite
Home in Chester
Riverfront Getaway
Dec 5 – 12
$159 per night
4.96 out of 5 average rating, 305 reviews
Guest favorite
Cabin in Becket
Waldtreff - quiet grand cabin
Sep 19 – 26
$219 per night
5.0 out of 5 average rating, 253 reviews
Guest favorite
Home in Hadley
Large Family Home Near Five Colleges
Apr 25 – May 2
$976 per night
4.96 out of 5 average rating, 47 reviews
Cottage in Becket
Berkshires Cottage Retreat - Private Hot Tub
May 16 – 23
$144 per night
4.67 out of 5 average rating, 333 reviews
Home in Amherst
"The House"
Jan 4 – 11
$988 per night
4.82 out of 5 average rating, 17 reviews

Family- and pet-friendly home rentals

Superhost
Guest suite in Northampton
Private Guest House Downtown Noho
Mar 20 – 25
$125 per night
4.76 out of 5 average rating, 825 reviews
Guest favorite
Apartment in Northampton
Cedar Wet Room w Soaking Tub
Apr 9 – 16
$150 per night
4.95 out of 5 average rating, 217 reviews
Superhost
Apartment in Ashfield
Zachariah House Main St. Ashfield
Sep 25 – Oct 2
$140 per night
4.86 out of 5 average rating, 213 reviews
Guest favorite
Home in New Salem
Stone n' Sky Lodge
Mar 29 – Apr 5
$200 per night
4.88 out of 5 average rating, 198 reviews
Guest favorite
Loft in Northampton
Light-filled Studio Apt. Near Smith
Aug 27 – Sep 3
$150 per night
4.98 out of 5 average rating, 250 reviews
Guest favorite
Home in Sunderland
Iconic New England Home
Jun 5 – 12
$600 per night
4.96 out of 5 average rating, 112 reviews
Guest favorite
Home in Amherst
Classic New England Country House, 5 min to town
Jul 15 – 22
$681 per night
4.88 out of 5 average rating, 56 reviews
Superhost
Cottage in Becket
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Dec 9 – 16
$176 per night
4.76 out of 5 average rating, 136 reviews
Guest favorite
Home in Plainfield
Pond & nearby Berkshire East Skiing w/ fireplace
Apr 27 – May 4
$264 per night
4.73 out of 5 average rating, 147 reviews
Guest favorite
Home in Shelburne Falls
Tulsi Rose Healing Retreat
Jan 27 – Feb 3
$428 per night
4.84 out of 5 average rating, 86 reviews
Guest favorite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
Sep 3 – 10
$211 per night
4.91 out of 5 average rating, 246 reviews
Guest favorite
Apartment in Whately
Historic stay near five colleges
Aug 17 – 24
$142 per night
4.85 out of 5 average rating, 163 reviews

Family-friendly home rentals with a pool

Guest favorite
Bungalow in Easthampton
The Creation Station
May 20 – 27
$131 per night
4.92 out of 5 average rating, 417 reviews
Guest favorite
Apartment in Northampton
Sunny Inspirit Apartment in best downtown location
Jun 6 – 13
$175 per night
4.97 out of 5 average rating, 230 reviews
Guest favorite
Apartment in Deerfield
Nestled Inn
Apr 11 – 18
$143 per night
4.93 out of 5 average rating, 54 reviews
Guest favorite
Apartment in Northampton
1880s sun-bathed beauty in best downtown location
Jul 23 – 30
$226 per night
4.96 out of 5 average rating, 270 reviews
Guest favorite
Apartment in Northampton
Light-bathed 3br w porch in best downtown location
Apr 30 – May 7
$212 per night
4.94 out of 5 average rating, 157 reviews
Guest favorite
Apartment in Northampton
Wood, sunshine & movies in best downtown location
Jul 5 – 12
$210 per night
4.96 out of 5 average rating, 199 reviews

Destinations to explore