Family-friendly vacation rentals in Western Massachusetts
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Western Massachusetts
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 Western Massachusetts family-friendly rentals
Family-friendly home rentals with a hot tub
Cottage in Shaftsbury
4.99 out of 5 average rating, 605 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Cabin in Saugerties
4.86 out of 5 average rating, 176 reviewsContainer Cabin in the Catskills (Field)
Home in Northampton
4.88 out of 5 average rating, 571 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Bungalow in Easthampton
4.92 out of 5 average rating, 437 reviewsThe Creation Station
Cabin in Monterey
4.95 out of 5 average rating, 252 reviewsAmazing Berkshire Mountains Cabin
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in Colrain
4.94 out of 5 average rating, 157 reviewsSecluded Farmhouse Retreat - stunning views
Apartment in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
Family- and pet-friendly home rentals
Guesthouse in Stephentown
5.0 out of 5 average rating, 364 reviewsDog Friendly Studio
Home in Feeding Hills
4.89 out of 5 average rating, 887 reviewsFarm Fresh Feeding Hills
Farm stay in Southbridge
4.89 out of 5 average rating, 296 reviewsScandanavian Wigwam with Sauna and Forest Baths
Loft in East Nassau
4.99 out of 5 average rating, 154 reviewsDog Friendly Farm Spring bird watching
Apartment in Newfane
4.97 out of 5 average rating, 407 reviewsRock River Retreat: Pets Welcome
Yurt in Pattersonville
4.99 out of 5 average rating, 784 reviewsMariaville Goat Farm Yurt
Farm stay in West Simsbury
4.95 out of 5 average rating, 438 reviewsFlamig Farm Staycation
Apartment in Northampton
4.95 out of 5 average rating, 220 reviewsCedar Wet Room w Soaking Tub
Family-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Home in Ghent
4.87 out of 5 average rating, 272 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Farm stay in Rutland
4.97 out of 5 average rating, 319 reviewsFarm Living
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in New Paltz
4.98 out of 5 average rating, 440 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Cheshire
5.0 out of 5 average rating, 119 reviewsPool House
Destinations to explore
- Cambridge Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Providence Vacation rentals
- Catskill Vacation rentals
- Albany 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 New York
- Family-friendly rentals New Hampshire
- Family-friendly rentals Massachusetts
- Kid-friendly rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Private suite rentals Western Massachusetts
- Rentals with beach access Western Massachusetts
- Monthly Rentals Western Massachusetts
- Rentals with a washer and dryer Western Massachusetts
- Hotel rentals Western Massachusetts
- Townhouse rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
- Cottage rentals Western Massachusetts
- Condo rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a home theater Western Massachusetts
- Wheelchair accessible rentals Western Massachusetts
- Waterfront rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Rentals with pools Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Boutique hotel rentals Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Chalet rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- House rentals Western Massachusetts
- Farmstay rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Vacation home rentals Western Massachusetts
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes