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.

Very nice home, amenities were top notch. Definitely a good find if you're looking to stay in the area!

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.

Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.

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!

What a beautiful place! Melissa and George were great hosts that think of all the details. When Airbnb got started we felt this was the exact vibe they were going for. It was authentic to cape cod culture and made us feel right at home. There is a little history book on the table that is worth the read and they also left us a booklet with current activities. We loved our stay and would definitely recommend it to others!

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.

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!

We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!

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

We stayed for a girls trip and it was absolutely perfect. The pool was amazing, so much space and balconies were incredible. The team was so responsive to lots of my questions leading up. The only challenge was parking, and the town of Dennis does not allow overnight parking so it’s park at your own risk. We found a park and ride in harwich and used that, so for those in the future with more than 3 cars. Would definitely stay again!

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

Perfect stay - just be sure to bring or order sheets and towels!

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.

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

Sara's place was fantastic! Perfect for our group running a local race. Walkable to Easton's Beach and restaurants in Middletown. the place is extremely comfortable and had everything we needed. Sara was excellent: very responsive and accommodating - I would definitely stay here again!