
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
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Popular amenities for Windham family-friendly rentals
Family-friendly home rentals with a hot tub

Hopkinton Mass 3+ Bedrooms - Great location!
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.

Hampton 100 yards to beach
Clean and good storage for a small space. Good location

Beach Dreaming
Great place to stay in Ogunquit area! The cottage is exactly as described, and well located between Wells and Ogunquit - you do need a car to get around easily as others have said. This is a fantastic place to stay with kids - having the pool facilities especially is great as a break from the beach. Julie and Derek left great advice as well as flexibility on check-in - thanks again!

Timothy House
This cabin was a little slice of heaven! Just what my boyfriend and I needed to refresh and recharge! The house was wonderful and everything was clean, spacious, and well labeled.

Seacoast Oasis (NH & ME)
Was my second stay, this time to celebrate my birthday with my partner and we had such a nice time! It’s a cozy, very clean and comfortable spot with an awesome hot tub and adorable ducks - Peter even gave us some delicious duck boiled duck eggs to sample. Highly recommend this Airbnb. We look forward to returning very soon!

Home On The Hill
Bryan and Monica are excellent hosts and myself and those who stayed had an awesome experience over the course of the 6 weeks we spent at their location. We would highly recommend staying at their properties and plan on spending more time in the area again soon.

awesome private cabin
Gorgeous grounds and location for a quiet peaceful weekend getaway! David was very responsive and personable. The cabin is eclectic with something new and interesting in every corner.

Sunrise Sunset Lakefront Suite
In the area for work. Absolutely loved the place. Would absolutely stay again for work or vacation.
Family- and pet-friendly home rentals

Welcoming 7-room house <15 miles to Boston & Salem
Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃

The Solar Powered Dogtown Cabin at Applecart Farm
Our stay at Dogtown Cabin was absolutely wonderful! Julie was consistently available for any questions or concerns and she was kind and welcoming and made sure we had everything we needed. The cabin itself was cozy yet spacious. Plus it was equipped with everything we needed to help make our stay comfortable. They had some great trails on the property and my family had a great time exploring them. The beautiful property is serene and private but close enough to a lot of tourists destinations. And let’s not forget the animals! My son had a great time meeting the horses and chickens. But I will say hands down the best part of our stay were our adorable furry hosts, Darwin and Azore! They greeted us every morning! Hanging out with them made our stay even more special! We honestly can’t wait to come back.

Family Home + Near Downtown + Cool Backyard!
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.

Charming South End Duplex (Pets Ok)
We just a wonderful few days in Boston for the marathon. Maude was the perfect host… we really appreciated the flexibility with check-in and check-out and were so grateful for the provisions left for us, particularly as we arrived late! The location is perfect, it meant that we could explore everywhere in the City on foot. The neighbourhood is particularly great for restaurants and when the sun came out and the temperature rose, the vibe was fabulous. As a previous review mentioned, if you’re looking for a pristine, freshly painted apartment then it’s not for you, but if you like ‘quirky’ and a house with bags of character, (I especially loved the art), then I’d highly recommend.

Family Friendly 2BR 1 BA Coastal Kittery Home
I booked the house as a place for my family of 6 (4 adult children) and our black lab, to come together for Easter weekend. Since my boys live in Portsmouth we only needed 2 bedrooms and this house made the perfect getaway and place to host dinners. The house was spacious and very comfortable. We enjoyed the enormous fenced in yard all weekend. The host had many yard games which we played and our lab was so happy too. The fire pit was an added bonus for a night of s’more making. We truly had a wonderful time and the house really felt like home. Ps the stairs are fine once you get used to them. Rebecca was responsive and a wonderful host.

Fire Fly Yurts on Funky Bow Lane
Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

Cambridge Getaway @ Harvard & MIT
This is an authentic Cambridge home that has been owned by the host's family for multiple generations. Kevin is accommodating, and he generously left some snacks and drinks in the full kitchen for us. Well-stocked kitchen was super convenient for eating breakfasts. Note: there are significant stairs to get into the unit. Once there it's quite spacious. And I love the operable bathroom window. :) Thanks for a lovely stay in a convenient, walkable neighborhood!

Comfortable house, close to beach and downton IPSW
This is our 3rd stay at one of their Airbnb’s and they are always so accommodating. Places are always clean and well stocked. Communication is great! Will Be staying again on our next visit!
Family-friendly home rentals with a pool

Luxury Ultra Modern House in Newton ; Boston
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!

Two-Bedroom Condo on the Wells/Ogunquit town-line
100 percent recommended!!

Farm Living
This was a wonderful stay for myself, daughter and two rambunctious grandsons. We all loved the farm experience and enjoyed visiting the animals... peacock, rabbitts, chickens galore, ducks, goats, donkeys, horses and cows! The trampoline and two playstructures plus sand box were fantastic! The hosts, Roger and Melissa, were very welcoming and encouraged us to explore. Having the farm store right on the property was a bonus!

Country Cottage in the City
Lovely place to stay, very peaceful. Mark and Merry were great hosts! Thank you very much!

Beautiful Beach Studio
Rita was responsive, friendly, and accommodating. Place was clean and inviting, close to the strip. Would definitely stay again!

Spacious 3-BR Furnished Beach Home
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!

Beautiful Lakefront Vacation
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.

Appledore Cottage is a Family Vintage Cottage
We absolutely loved our visit to Appledore Cottage! It was quaint and perfectly relaxing. The screened in porch was the best place to just sit…very quiet and peaceful!
Quick stats about vacation rentals that are family-friendly in Windham
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.5K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Hampton Beach
- Wells Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Ogunquit Playhouse
- Long Beach
- New England Aquarium
- Pats Peak Ski Area
- Monadnock State Park
- Faneuil Hall Marketplace
- Long Sands Beach
- Freedom Trail
- Prudential Center
- Symphony Hall
- Boston Public Library
- Crane Beach
- Rye North Beach
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market