Family-friendly vacation rentals in Windham County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham County
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 Windham County family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
Home in Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
Chalet in Dover
4.97 out of 5 average rating, 104 reviewsGrey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Home in Jamaica
4.96 out of 5 average rating, 47 reviews4 Bedroom on 90 Acres in the mountains of Vermont!
Home in Dover
4.97 out of 5 average rating, 75 reviewsWonderful House! Rec Room HotTub Firepit Garden!
Home in Peru
4.63 out of 5 average rating, 56 reviewsNorman Rockwell Spacious Contemporary + Hot Tub
Family- and pet-friendly home rentals
Loft in Wilmington
4.92 out of 5 average rating, 172 reviewsWalk to Village/Lake Whitingham
Home in Newfane
4.95 out of 5 average rating, 172 reviewsAdorable home in Newfane
Home in Guilford
4.94 out of 5 average rating, 175 reviewsPeaceful Country Home
Home in Dummerston
4.99 out of 5 average rating, 324 reviewsPinecone Pond
Home in Putney
4.85 out of 5 average rating, 233 reviewsPreston’s Pond-Beautiful home on Tranquil Hilltop
Cabin in Jamaica
4.88 out of 5 average rating, 266 reviewsGreen Mountain Modern House: iconic modern getaway
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
Chalet in Readsboro
4.86 out of 5 average rating, 286 reviewsThe King's Cottage
Family-friendly home rentals with a pool
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
Townhouse in Dover
4.93 out of 5 average rating, 71 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
Cottage in Dover
5.0 out of 5 average rating, 14 reviewsLuxury King, fireplace, pvt entrance- Farmhouse 1
Chalet in Wilmington
4.94 out of 5 average rating, 89 reviewsRustic Sunny Vermont Home near Mount Snow
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Family-friendly rentals Vermont
- Family-friendly rentals New York
- Family-friendly rentals New Hampshire
- Rentals with beach access Windham County
- House rentals Windham County
- Rentals with pools Windham County
- Beachfront rentals Windham County
- Apartment rentals Windham County
- Rentals with a sauna Windham County
- Cabin rentals Windham County
- Ski-in/ski-out rentals Windham County
- Fitness-friendly rentals Windham County
- Rentals with a fireplace Windham County
- Rentals with a patio Windham County
- Rentals with a kayak Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Guesthouse rentals Windham County
- Tiny house rentals Windham County
- Bed and breakfasts Windham County
- Monthly Rentals Windham County
- Rentals with a fire pit Windham County
- Rentals with an accessible height toilet Windham County
- Rentals with outdoor seating Windham County
- Pet-friendly rentals Windham County
- Rentals with lake access Windham County
- Rentals with a hot tub Windham County
- Rentals with a washer and dryer Windham County
- Chalet rentals Windham County
- Rentals with an EV charger Windham County
- Private suite rentals Windham County
- Rentals with breakfast Windham County
- Farmstay rentals Windham County
- Townhouse rentals Windham County
- Condo rentals Windham County
- 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