Family-friendly vacation rentals in Windham

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Windham family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars5 days ago
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.
Guest favorite
Condo in Hampton Beach
4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

KrystinaRating, 5 stars8 months ago
Clean and good storage for a small space. Good location
Superhost
Cottage in Wells
4.88 out of 5 average rating, 41 reviews

Beach Dreaming

StevenRating, 5 stars7 months ago
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!
Guest favorite
Home in Tilton
4.93 out of 5 average rating, 471 reviews

Timothy House

CarolynRating, 5 stars2 days ago
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.
Guest favorite
Guest suite in Kittery
4.91 out of 5 average rating, 834 reviews

Seacoast Oasis (NH & ME)

LeeRating, 5 stars6 days ago
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!
Guest favorite
Home in Dunbarton
4.9 out of 5 average rating, 30 reviews

Home On The Hill

RileyRating, 5 stars2 months ago
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.
Guest favorite
Cabin in Rochester
4.94 out of 5 average rating, 228 reviews

awesome private cabin

IlonaRating, 5 stars6 months ago
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.
Guest favorite
Place to stay in Hampstead
4.88 out of 5 average rating, 91 reviews

Sunrise Sunset Lakefront Suite

EdwardRating, 5 stars5 months ago
In the area for work. Absolutely loved the place. Would absolutely stay again for work or vacation.

Family- and pet-friendly home rentals

Top guest favorite
Home in Wakefield
4.96 out of 5 average rating, 260 reviews

Welcoming 7-room house <15 miles to Boston & Salem

TyroneRating, 5 stars1 week ago
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. 😃😃
Top guest favorite
Cabin in Rockport
4.97 out of 5 average rating, 447 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

AnaisRating, 5 stars1 week ago
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.
Guest favorite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars1 month ago
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.
Guest favorite
Apartment in South End
4.96 out of 5 average rating, 374 reviews

Charming South End Duplex (Pets Ok)

HelenRating, 5 stars5 days ago
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.
Top guest favorite
Home in Kittery
4.98 out of 5 average rating, 286 reviews

Family Friendly 2BR 1 BA Coastal Kittery Home

ChristineRating, 5 stars5 days ago
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.
Guest favorite
Yurt in Lyman
4.93 out of 5 average rating, 262 reviews

Fire Fly Yurts on Funky Bow Lane

KaylaRating, 5 stars6 months ago
Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive
Guest favorite
Apartment in Cambridge
4.87 out of 5 average rating, 438 reviews

Cambridge Getaway @ Harvard & MIT

LindaRating, 5 stars1 month ago
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!
Superhost
Apartment in Ipswich
4.85 out of 5 average rating, 279 reviews

Comfortable house, close to beach and downton IPSW

Zachary AndrewRating, 5 stars1 week ago
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

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars40 months ago
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!
Guest favorite
Condo in Wells
4.84 out of 5 average rating, 178 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

EverRating, 5 stars2 weeks ago
100 percent recommended!!
Top guest favorite
Farm stay in Rutland
4.96 out of 5 average rating, 362 reviews

Farm Living

GinaRating, 5 stars2 weeks ago
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!
Top guest favorite
Guesthouse in West Roxbury
4.95 out of 5 average rating, 192 reviews

Country Cottage in the City

BeckyRating, 5 stars5 months ago
Lovely place to stay, very peaceful. Mark and Merry were great hosts! Thank you very much!
Superhost
Apartment in Hampton Beach
4.74 out of 5 average rating, 121 reviews

Beautiful Beach Studio

AngelaRating, 5 stars8 months ago
Rita was responsive, friendly, and accommodating. Place was clean and inviting, close to the strip. Would definitely stay again!
Guest favorite
Home in Hull
4.96 out of 5 average rating, 23 reviews

Spacious 3-BR Furnished Beach Home

BriannaRating, 5 stars10 months ago
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!
Guest favorite
Home in Derry
4.83 out of 5 average rating, 134 reviews

Beautiful Lakefront Vacation

BobRating, 5 stars7 months ago
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.
Superhost
Cottage in Wells
4.64 out of 5 average rating, 102 reviews

Appledore Cottage is a Family Vintage Cottage

PamelaRating, 5 stars7 months ago
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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