Family-friendly vacation rentals in Chilmark

We stayed here for a bachelorette party and the house exceeded our expectations. Sherri was responsive and quick to answer all of our questions before and during the stay.

Had a lovely stay here! It’s a really beautiful, charming location close to lots of great shops and restaurants.

Dennis was easy to communicate with and answered my questions promptly. Dennis was very helpful. The house was clean and close to the village. The rainy day was saved by the board games provided, creating new memories. Outstanding decorations. Highly recommend this super host! :)

The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.

Came here for my sisters bachelorette. It was amazing . We felt right at home . It was very spacious and clean . Hosts thought of everything . Definitely would come back. The hosts were very responsive and very flexible. Great place to stay. The games and ping pong and air hockey tables were a hit !!

The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!

This was our second time renting this property. We had a lovely adults weekend, and really enjoyed our stay.

Location was great and the neighborhood was quiet and beautiful. Robert was very responsive and accommodating. The ease of finding the home & access with the great directions along with a bottle of wine in the fridge were added bonuses after driving all day/night and a late night arrival.

This was exactly what we were looking for--it was equal distant from vineyard haven and oaks bluff, right along the bus route. We ended up renting bikes and biking to and from different towns, which was amazing. Theda was extremely responsive and even let us check in and out when we needed. We'll definitely stay here again when we're in town!

My husband and I were transferred to a project about 30 minutes from Olga’s home. After a very long drive from WV we were pleasantly surprised. Olga’s property was exactly as described. Given we were there for an extended stay it was refreshing to find a fully stocked kitchen with high-end appliances. The master bedroom and ensuite exceeded our expectations: the room was quite large, the mattress was comfy, it offered a build in desk and private patio doors that led to the back yard. My favorite, was the very large soaking/jetted tub after a long cold day. We were overjoyed that not only did she permit dogs, she had a huge fenced in yard do”so even our Ralphie was happy. As if things could get any better we walked to the beach nearly everyday. Did i mention its only 0.2 miles away. PS: Craigsville pizza and Mexican is the bomb!!

We drove up and thought it was going to be a tight fit for 3 adults, 2 teens and dogs, but we were wrong. We walked in and the first thing I notices was how clean and fresh it smelled. It was amazing! The place was spotless, the sofa was comfy, the area was great but the real show stopper....the view. Right on flax pond with gorgeous sunrises and relaxing evenings. My guys fished right from the deck....it was the perfect spot. Meg was amazing to work with as well. No surprises. Meg checked in leading up to the visit and after we left, but made sure we knew she was only a call away if we needed anything during our stay. Thank you Meg!

This is the third time my family has stayed in this beautifully furnished and extremely comfortable home, located on a quiet cul de sac. Always perfect for our Vineyard get-aways.

I truly cannot say enough good things about Kristen and her home! The photos do not do the home justice. As soon as we walked in we were completely at home. This is do in great part to Kristen's joy in communicating with us. It was quite evident that she wanted our stay to be perfect and she was willing to do whatever we needed to make it a great stay! Thank you Kristen for your warmth and hospitality!

We loved this Airbnb! It was perfect for our family of 4 adults and 2 children. One of the bedrooms had lots of books which the kids loved. The kitchen had almost everything you’d need to make meals. We made quite a few! The record player is great. The couch is so comfy. We would totally stay here again!

Had a great stay at this lovely cottage. Came equipped with everything you’d need and was super clean. Comfortable furniture and bed was a plus. We also enjoyed the fireplace at night. The backyard was a peaceful spot to enjoy morning coffee and listen to the birds. Beaches are close by as well as many great restaurants or shopping. Would recommend and stay again

A magical spot indeed! We stayed for 4 perfect nights and we enjoyed ourselves immensely. The grounds are very pretty, with wild turkeys visiting for morning coffee. The kitchen is newly remodeled and stunning. The pool was a great find and there were plenty of nice towels and an outdoor shower. The host is lovely and the caretaker called to say hello as well so we felt very taken care of. A must visit! 10 stars!

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!

What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.

The home was pristine, more than what we could have asked for. Shelly was an amazing host, again, more than we could have asked for. You want a gorgeous home, with a stellar host, in the cape, with a private pool, amazing amenities, on a golf course and very close to the beaches, fun spots for kids, and shops, go to this place.

Good location ! Plenty to do and friendly service. I’d use them again

We had a wonderful weekend stay! The house is located in a quiet neighborhood and the upstairs apartment was very clean. There is quick access to local beaches and restaurants. We would stay again!

Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience