Family-friendly holiday 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.
Holiday 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
Treehouse in Georgetown
4.98 out of 5 average rating, 404 reviewsModern Tree Dwelling w/Water Views+Cedar Hot Tub
14–21 Dec
Home in Waterford
4.83 out of 5 average rating, 217 reviewsMcWain pond house (private lake & hot tub)
3–10 Jun
Flat in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
6–13 Sep
Guest suite in Kittery
4.9 out of 5 average rating, 744 reviewsSeacoast Oasis (NH & ME)
Home in Tilton
4.94 out of 5 average rating, 422 reviewsTimothy House
16–23 Apr
Flat in Biddeford
4.98 out of 5 average rating, 118 reviewsBrenda and Phil's Place
27 Feb – 6 Mar
Apartment in Laconia
4.9 out of 5 average rating, 331 reviewsMillion Dollar View! Weir's Beach 1/4 mile away!
29 Mar – 5 Apr
Guest suite in Kittery Point
4.94 out of 5 average rating, 233 reviewsHot Tub & Spa-Like! Pamper Yourself This Spring!
8–15 Apr
Family- and pet-friendly home rentals
Farm stay in Scarborough
4.85 out of 5 average rating, 214 reviews434 Acres and a Cabin
9–16 Mar
Cabin in Windham
4.91 out of 5 average rating, 193 reviewsPrivate Hilltop Cabin, Lakes and Trails Abound..
19–26 Aug
Cottage in Gray
4.9 out of 5 average rating, 190 reviewsSunset Haven - Little Sebago Lake
24–31 Oct
Flat in Harpswell
4.83 out of 5 average rating, 240 reviewsSunny Apartment on the Ocean.
15–22 Dec
Flat in Lisbon falls
4.95 out of 5 average rating, 383 reviewsCharming Victorian farmhouse 1880's bedrooms-2
27 Apr – 4 May
Home in Paris
4.94 out of 5 average rating, 129 reviewsJust a get away!!
26 Dec – 2 Jan
Guest suite in Brunswick
4.93 out of 5 average rating, 315 reviewsArt House Gallery guest suite
16–23 Jan
Barn in Naples
4.85 out of 5 average rating, 172 reviewsPeace on High, Entire home throughout your stay!
10–17 Nov
Family-friendly home rentals with a pool
Flat in Brunswick
4.99 out of 5 average rating, 194 reviewsCharming Saltwater Farm apartment
26 Oct – 2 Nov
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
23–30 Aug
Apartment in Bartlett
4.72 out of 5 average rating, 201 reviewsExcellent Getaway in N.Conway area!
13–20 Sep
Apartment in Intervale
4.93 out of 5 average rating, 147 reviewsUpscale retreat w/ panoramic White Mountain views
24 Apr – 1 May
Apartment in Waterville Valley
4.76 out of 5 average rating, 316 reviews🔷 Cozy Ski Condo 🔷
1–8 Oct
Home in Kennebunk
4.81 out of 5 average rating, 114 reviewsKennebunk/Kennebunkport Beach House w/Pool!
20–27 Oct
Apartment in Wells
4.84 out of 5 average rating, 145 reviewsNew Condo on the Wells/Ogunquit town-line
20–27 Jan
Apartment in Bartlett
4.85 out of 5 average rating, 251 reviewsAttitash Studio | 5min to Storyland| Pools
8–15 Oct
Quick stats about holiday 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
$122 SGD before taxes and fees
Destinations to explore
- Portland Holiday rentals
- Salem Holiday rentals
- Chebacco Lake Holiday rentals
- Old Orchard Beach Holiday rentals
- Lake Winnipesaukee Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Québec City Holiday rentals
- Québec Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Maine
- Family-friendly rentals New Hampshire
- Family-friendly rentals Portland
- Family-friendly rentals Salem
- Cottage rentals Windham
- Beachfront rentals Windham
- Rentals with a fireplace Windham
- Rentals with a washing machine and dryer Windham
- House rentals Windham
- Family-friendly rentals Windham
- Rentals with outdoor seating Windham
- Rentals with a firepit Windham
- Rentals with beach access Windham
- Rentals with lake access Windham
- Waterfront rentals Windham
- Monthly Rentals Windham
- Rentals with a kayak Windham
- Rentals with a patio Windham
- Pet-friendly 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