
Family-friendly holiday rentals in Windham
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Top-rated family-friendly rentals in Windham
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Family-friendly home rentals with a hot tub

Attitash Studio | 5min to Storyland| Pools
Was a nice peaceful stay for the most part. The pools were nice to swim in although it seems not everyone seemed to want to follow the pool rules. Doesn't help that there were no lifeguards to ensure kids remained safe other than the parents. A few times I saw individuals in the pool water with either glass or an open drink in hand. Saw kids diving into the pool and even witnessed a few hurt themself. But other than that, the hot tub was so lovely to soak in. The arcade room was fun to play in. It was cool to see there was a lot to be able to do in the area for yourself. Definitely wish there was more to do in the area other than the classic tourists spots. A lot of beautiful spots to hike. We ended up checking out Diana's Bath and it was a gorgeous spot to watch cascading waterfalls or have a tiny dip. Would definitely check out this space again and maybe spend a few more days to truly appreciate the environment and mountains ^-^

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim
we had a great time! the house was very clean and the location was perfect. just a short walk to the lake, which was very peaceful. the host was responsive and answered all of our questions.

Falmouth 3br near Town landing
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

Tree Dwelling with Water Views & Cedar Hot Tub (2)
Beautiful spot to stay at, we didn’t get so lucky with how weather panned out but it didn’t take away from the experience we had. Would recommend to anyone!

Attitash Retreat
Had a great time peaceful get-away with great mountain views. Climbing,swimming,snowboarding, and all outdoor sports within close distance. I would definitely stay again

Cozy hot tub haven
Wendy’s place was really nice and the hot tub is very private.. we definitely got our usage out of it… Wendy herself was extremely kind and open minded. She didn’t rush us out come check out, instead, she encouraged us to stay a little longer and enjoy the hot tub before our long journey back home.. she gave us good tips about golden gems only locals know about 🥰 She did have a cool book to share reviews but I didn’t have a pen.. also we left grape soda in the fridge from Canada for the next person to try!! Thanks again Wendy 5⭐️

Maine Lakes Region house (private hot tub)
The spot was perfect for a weekend of skiing and riding snowmobiles. Exactly what we were looking for in a vacation home. Paul was great at recommending places and his response time was great. Also the wood burning stove made the weekend cozy and perfect.

awesome private cabin
Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some
Family- and pet-friendly home rentals

Freeport Village Sunny Studio
We enjoyed our stay in the studio in Freeport. It was perfect for our needs, as we needed a place to stop for one night. It was incredibly clean, bright, with alot of natural light during the day. The bed was very comfortable! It was a short walk to the outlets, LL Bean, and nice restaurants and coffee shops. We would stay here again when visiting Freeport!

Private Hill Top Apartment/w One Car Driveway
Magical stay in a magical space. My family and I are do grateful for your hospitality.

McKeen's Riverside Retreat
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Gorgeous Studio on the Kennebec
Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

Island Glamping in a Luxury Tent in Maine
Incredible place. The island is beautiful, and everything is ready for you so you don't have much to do. Kent was great at communicating, gave us all the information we needed and was quick to help us, making the whole experience very easy. We will be back

New 2BR 2King beds Private Apt Downtown Brunswick
Great place to stay in Brunswick! Extremely walkable to the downtown restaurants and shops. Clean and bright space with spacious bedrooms (enough space to throw a pack-and-play in one of the bedrooms). Beds were comfortable and living room/kitchen good for socializing! Bonus — you can also access the Androscoggin River path for a nearby dose of nature and water. This is the second location of Spencer’s we’ve stayed in (the other about two years ago) and both stays were awesome. Highly recommend for a trip to Brunswick!

White Mt Retreat with New Kitchen and Beach Pass
The listing, the communication, the home, the location…all exceptional. Haven’t had a nicer place than this in a while. It was quiet and very comfortable. Minutes from great food, shopping, and things to love in the North Conway area. Very much recommended

Lake Region Comfort, Close to Everything!
Everything was great! Very close to the town center of Bridgton and the place had everything we needed. Loved the DVD collection and the beds were SO comfy!
Family-friendly home rentals with a pool

Upscale retreat w/ panoramic White Mountain views
We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

Storyland, golf, hiking, kayak and more
We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Across from Storyland & in the Heart of the Mtns
Beautiful place, has everything you might need. Very convenient location , close to storyland, restaurants and convenience stores . The restaurant recommendations from the host were great

Quiet Condo Close to Shopping and Attractions
Amazing place! Clean, lots of amenities, and the place had all the basics you could need! I will definitely be referring friends and returning for future trips!

Intimate Garden Style Condo with Mountain Views
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!

Bartlett N. Conway, NH condo ski near Storyland
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

*Chalet in the Sky|NorthConway+StoryLand|Outlets
Krysten's chateau was perfect for a family trip with my girlfriend, my sister and my sister's husband! The two bedrooms were very tidy and cozy and both bathrooms had plenty of towels and soaps. Krysten left thoughtful touches through the space such as a guide book with recommendations for places to visit, restaurants, and instructions for check in, check out, and how to use all of the amenities. the view from the back porch was beautiful and this made for a very cozy, yet spacious, place to rest after long days of hiking various trails (and Mt. Monroe) and visiting the surrounding areas, including North Conway. This space would be especially great for families with kids because there are board games included by the owner(s), bunk beds in the second bedroom as well as a second queen bed, and you would be in arms reach or Story Land! Overall, I would 10/10 recommend this AirBnb to anyone looking for an affordable, renovated, clean, and beautiful space for their trip to New Hampshire!
Quick stats about holiday rentals that are family-friendly in Windham
Total rentals
130 properties
Nightly prices starting at
₹7,754 before taxes and fees
Total number of reviews
4.8K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
130 properties include access to wifi
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Story Land
- Attitash Mountain Resort
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cranmore Mountain Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths