Family-friendly vacation rentals in Windham
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham
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 family-friendly rentals
Family-friendly home rentals with a hot tub
Guest suite in South Portland
5.0 out of 5 average rating, 684 reviewsOceanfront with amazing views and private entrance
Oct 24 – 31
Treehouse in Georgetown
4.98 out of 5 average rating, 404 reviewsModern Tree Dwelling w/Water Views+Cedar Hot Tub
Dec 15 – 22
Home in Waterford
4.83 out of 5 average rating, 218 reviewsMcWain pond house (private lake & hot tub)
Jan 30 – Feb 6
Apartment in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
Sep 2 – 9
Apartment in Biddeford
4.98 out of 5 average rating, 118 reviewsBrenda and Phil's Place
Mar 5 – 12
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMILLION$ views, HOT TUB, Crooked RIVER, 14 acres
Oct 8 – 15
Cottage in Conway
4.9 out of 5 average rating, 296 reviewsHOT TUB! Amazing view. Hike, Bike, Swim!
Oct 26 – Nov 2
Cabin in Jackson
4.84 out of 5 average rating, 786 reviewsCozy Log Cabin/Private Hot Tub/Brook/Fireplace
Mar 14 – 21
Family- and pet-friendly home rentals
Barn in Naples
4.85 out of 5 average rating, 172 reviewsPeace on High, Entire home throughout your stay!
Jul 10 – 17
Farm stay in Scarborough
4.85 out of 5 average rating, 214 reviews434 Acres and a Cabin
Feb 26 – Mar 5
Cottage in Gray
4.9 out of 5 average rating, 190 reviewsSunset Haven - Little Sebago Lake
Jan 24 – 31
Condo in Portland
4.86 out of 5 average rating, 330 reviewsBack Cove - Sunny 2nd Floor Condo
May 11 – 16
Home in Bath
4.89 out of 5 average rating, 284 reviewsGorgeous Summer Studio on the Kennebec
May 30 – Jun 6
Guest suite in Brunswick
4.93 out of 5 average rating, 315 reviewsArt House Gallery guest suite
Dec 10 – 17
Apartment in Harpswell
4.83 out of 5 average rating, 240 reviewsSunny Apartment on the Ocean.
Oct 13 – 20
Home in Paris
4.94 out of 5 average rating, 129 reviewsJust a get away!!
Dec 18 – 25
Family-friendly home rentals with a pool
Apartment in Brunswick
4.99 out of 5 average rating, 194 reviewsCharming Saltwater Farm apartment
Nov 23 – 30
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
Aug 27 – Sep 3
Condo in Bartlett
4.72 out of 5 average rating, 201 reviewsExcellent Getaway in N.Conway area!
Jan 12 – 19
Condo in Bartlett
4.85 out of 5 average rating, 251 reviewsAttitash Studio | 5min to Storyland| Pools
Oct 10 – 17
Condo in Intervale
4.93 out of 5 average rating, 147 reviewsUpscale retreat w/ panoramic White Mountain views
Jul 23 – 30
Condo in Wells
4.84 out of 5 average rating, 145 reviewsNew Condo on the Wells/Ogunquit town-line
Oct 19 – 26
Home in Kennebunk
4.81 out of 5 average rating, 114 reviewsKennebunk/Kennebunkport Beach House w/Pool!
Oct 20 – 27
Chalet in Bartlett
4.92 out of 5 average rating, 171 reviews*Summit Vista 2Bd Chalet|Story Land|N.Conway
Oct 8 – 15
Quick stats about vacation rentals that are family-friendly in Windham
Total rentals
130 properties
Wifi availability
120 properties include access to wifi
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Total number of reviews
4.2K reviews
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Destinations to explore
- Portland Vacation rentals
- Salem Vacation rentals
- Chebacco Lake Vacation rentals
- Old Orchard Beach Vacation rentals
- Lake Winnipesaukee Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Maine
- Family-friendly rentals New Hampshire
- Family-friendly rentals Portland
- Family-friendly rentals Salem
- Rentals with a fire pit Windham
- Rentals with a fireplace Windham
- Rentals with outdoor seating Windham
- Waterfront rentals Windham
- Beachfront rentals Windham
- Rentals with lake access Windham
- Rentals with a washer and dryer Windham
- Kid-friendly rentals Windham
- Pet-friendly rentals Windham
- Rentals with beach access Windham
- Cottage rentals Windham
- Rentals with a patio Windham
- Rentals with a kayak Windham
- House rentals Windham
- Monthly Rentals Windham
- Family-friendly rentals Cumberland County
- 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