Family-friendly vacation rentals in Pioneer Valley
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Pioneer Valley
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pioneer Valley family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Oct 14 – 21
Home in Northampton
4.87 out of 5 average rating, 567 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Sep 8 – 15
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
Feb 27 – Mar 6
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Mar 3 – 10
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 5 – 12
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
Nov 14 – 21
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
Jan 25 – Feb 1
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
Sep 19 – 26
Family- and pet-friendly home rentals
Guest suite in Northampton
4.76 out of 5 average rating, 836 reviewsPrivate Guest House Downtown Noho
Jul 16 – 21
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Mar 7 – 14
Apartment in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
Aug 19 – 26
Home in Feeding Hills
4.89 out of 5 average rating, 885 reviewsFarm Fresh Feeding Hills
Sep 2 – 9
Loft in Northampton
4.97 out of 5 average rating, 251 reviewsLight-filled Studio Apt. Near Smith
Nov 15 – 22
Farm stay in West Simsbury
4.95 out of 5 average rating, 432 reviewsFlamig Farm Staycation
Feb 6 – 13
Cabin in Brattleboro
4.89 out of 5 average rating, 442 reviewsCottage
Jun 14 – 21
Guesthouse in Stephentown
5.0 out of 5 average rating, 361 reviewsDog Friendly Studio
Jan 25 – Feb 1
Family-friendly home rentals with a pool
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
Jul 21 – 28
Apartment in Northampton
4.96 out of 5 average rating, 200 reviewsWood, sunshine & movies in best downtown location
Aug 17 – 24
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Jun 16 – 23
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Nov 24 – Dec 1
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Sep 22 – 29
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Oct 16 – 23
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 28 – Feb 4
Barn in Pownal
4.94 out of 5 average rating, 78 reviewsArtist Bunkhouse Southern Vermont
Jun 2 – 9
Destinations to explore
- Cambridge Vacation rentals
- Montauk Vacation rentals
- New Haven Vacation rentals
- Salem Vacation rentals
- Newport Vacation rentals
- Lake George Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Family-friendly rentals The Hamptons
- Family-friendly rentals New Hampshire
- Family-friendly rentals Massachusetts
- Cottage rentals Pioneer Valley
- Condo rentals Pioneer Valley
- Rentals with beach access Pioneer Valley
- Rentals with pools Pioneer Valley
- Private suite rentals Pioneer Valley
- Waterfront rentals Pioneer Valley
- Rentals with a kayak Pioneer Valley
- Rentals with a fireplace Pioneer Valley
- Rentals with a fire pit Pioneer Valley
- Monthly Rentals Pioneer Valley
- Cabin rentals Pioneer Valley
- Kid-friendly rentals Pioneer Valley
- Fitness-friendly rentals Pioneer Valley
- Pet-friendly rentals Pioneer Valley
- Rentals with outdoor seating Pioneer Valley
- Rentals with a patio Pioneer Valley
- Rentals with a washer and dryer Pioneer Valley
- House rentals Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Smoking-friendly rentals Pioneer Valley
- Apartment rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
- Rentals with an EV charger Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom