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.

We had a great weekend here. The entire house was very well clean when we arrived. The kitchen had everything we needed and the table was large enough to fit our entire group. We had a great time relaxing in the hot tub and game room. We would definitely recommend and book again.

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

We had a wonderful week staying at Melissa and George’s Airbnb. The place was the perfect size for our family, a great place to hang out in between activities and had everything we needed. The screened in porch was heavenly and perfect for drying wet stuff from the beach. Lots of great amenities (chairs, boogie boards, etc) to use as well for our many trips to the beach and nearby lakes. Plenty of games to choose from too. The foosball table in the basement was a nice bonus. The hosts gave helpful recommendations and there was plenty of fun things to do within a short drive. Would highly recommended this place!

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!

We stay here often when visiting the Cape. Aruna is an amazing host and her home is lovely! I would definitely recommend staying here!

Lia and Michael are great hosts, so friendly and went out of their way to be accommodating and helpful to us! We had a great stay, their cottage is beautiful and we hope to be back again soon!

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 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!

We loved our weekend at Karen's place! The house was cozy and clean, and had everything we needed for a comfortable stay (including treats for our pup)! The yard and deck were nice and private, and the house was conveniently located to many restaurants, shops, and not far from the water. Karen made us feel right at home!

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

We loved our stay! The house is super family-friendly, the pool was amazing, and we found the house very cozy. There were plenty of cooking utensils/pots, which made cooking easy and a great grill and fire pit. Communication with Joe was super easy too.