Family-friendly holiday rentals in Windham

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.

Clean and good storage for a small space. Good location

A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

Large, bright, spacious beach house just steps from the beach and a short walk from the more bustling areas of OOB. Ocean views from all floors. Spacious enough for groups to be together but also to have some privacy if need be. Comfortable beds and well stocked kitchen. Lovely patio with spacious hot tub, outdoor dining area and small yard. A great spot with a responsive host!

Spacious and functional accommodation. 2 large bedrooms and a small living room, plus a kitchen. Quiet. A few noises upstairs but nothing very inconvenient.

We enjoyed the our stay. The house has unique design, kids love it! A very relaxing home like place. Bryan is super responsive and friendly. The house is well equipped with everything we need. Can’t ask for more. Thank you!

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.

In the area for work. Absolutely loved the place. Would absolutely stay again for work or vacation.

We really enjoyed our stay here! Karen was very quick to respond to any of our questions. The house is spacious and clean. We especially enjoyed the kitchen and dining room. I’d recommend this place to anyone staying in the area!

We loved our stay at Dogtown cabin. The cabin is in the middle of the woods and is also close to everything. Azure and Darwin are excellent hosts. Thank you Eric and Julie for sharing your home!

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.

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.

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.

Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

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!

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!

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!

Had a wonderful stay at Christophers place. He is a great host, always responsive with clear instructions. Place was peaceful, private and is exactly same as it was in the pictures. Will come soon!

You can’t beat Roger and his family’s hospitality or the outside amenities for children(farm, 2 playscapes, walking trails, etc). Truly a unique experience and must stay for families.

Lovely cottage surrounded by countryside: there were ducks, wild turkeys, chipmunks and blue jays in the garden. 5 mins drive from the lovely town of Dedham and 30 mins into central Boston. Cottage is small but beautifully decorated and has everything you need. Mark was super helpful.

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

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!

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

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!