House holiday rentals in Chilmark

We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.

We had a wonderful stay here in New Seabury! The house is beautiful, spacious and just as described. The heated pool was an added bonus! Michael provided prompt and clear communication when needed. I would absolutely stay here again!

We had such a fantastic stay at Sue’s beautiful Edgartown home! The house was charming, spotless, and well-stocked with everything we needed—from kids’ toys and extra keys to cozy spaces for the whole family. Even with some chilly weather, we made great memories thanks to Sue’s warmth and hospitality. One huge highlight was the car rental—what a convenient bonus! It was clean, reliable, and made exploring the island a breeze. Sue was responsive and thoughtful throughout our stay, checking in with helpful suggestions and going above and beyond. She truly made us feel at home. From shell picking at Felix Neck to relaxing in the playroom and enjoying everything the Vineyard has to offer, our family had a wonderful time. We’re already talking about our next trip back—and hoping Sue’s hot tub addition is ready by then! Highly recommend!

This home was great for our family. The pool and backyard are beautiful, and the house was clean and welcoming. There are a lot of activities in the area. I would stay here again!

Our family just had a wonderful time at Stacy and Mario‘s house. The house was immaculate, comfortable and extremely well appointed. The views were beautiful especially the sunsets. The hosts were extremely responsive and considerate

Wonderful place to stay! So comfortable and lots of space! Close to lots of restaurants and shopping! Would definitely stay again!

Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend

Great space for a group of people to hang out at for a weekend. Plenty to do in the area. Beds were comfortable. First Airbnb I have stayed at that had bidets installed in all of the bathrooms which was a nice perk

What a wonderful stay we had! The house was stocked with anything you could think of and the host Caroline was readily available for any questions. Will absolutely come back and recommend to all!

This property is on another level. It’s the four seasons of Airbnb. It’s such an immaculate place to stay and we loved every part of it. The cleanliness, the high quality of the essentials, the coziness, ambience and so much more was truly worth the stay.

We loved the location at the end of a little road so no through traffic (fresh eggs next door too). The pond is fun with lots of wildlife, sometimes we could hear the roosters next door. The sunsets are lovely from the home as well. Seating in the living room great and found it to be quiet when sleeping at night. The two bedrooms on the lower level both have heat pumps (for heat/cooling) we have always had great luck with (for temperature control in the bedrooms). Loved sitting on the back deck and having the resident geese wandering around. Lovely property!

We traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.

Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!

This is a lovely old family home that has been updated with all the modern kitchen and bathroom conveniences you need. Very cute cottage feel, lovingly maintained and updated just enough over the years. Our group included three couples with kids, and the many rooms were perfect for us. One note is that the full bed described is a bit more of a daybed so kind of small, but still cozy. Great house for a family with kids. Really pretty landscaping too and a lovely back deck. Would stay again!

Truly the best Airbnb experience I have had. Hosts are kind and thoughtful. They made sure we had everything we needed. House is spotless. Beds very comfortable. Perfect location with the beautiful water view. Great restaurants around. And easy trip to Boston from the local train station just 10 mins away! We hope to come back soon!!!

Fair Heaven is exactly that, a peaceful, quiet town with salty breezes, great restaurants, and the ocean at our door offers a calming surf. It doesn’t get any better than that!

We had such a nice time staying in this home! It was beautifully decorated and was extremely clean. We felt right at home during our visit. We had a hiccup at the start of our stay but our host was very quick responsive. I really enjoyed my stay and hope to be back

We have stayed at Brian’s place two years in a row, and it is by far the best airbnb we have ever stayed at. We love the amenities! Also, it is always incredibly clean and has super comfortable beds. Brian is incredibly responsive and accommodating, overall, an amazing host! We highly recommend staying here and plan to come back again!

Lovely spot near end of a cul de sac, great water views and light. Joel was proactive and responsive in communication.

We stayed over the long weekend at this beautiful property. It’s located centrally close to all the major attractions and beaches. The property had beautiful features and felt very comfortable. The home itself had a lot of charm and had a positive energy. Hosts were very kind and nice to communicate with. They left us wonderful treats and fresh eggs from their beautiful garden. Overall it was a great stay at their property. Highly recommended and we will be staying there again. I will highly recommend getting a car to travel in the island so you can go to Edgartown or other places.

Liza’s place is magical. The house is so much more than a beach house. It has a soul! Thank you Liza for being such an exquisite host.

We stayed here for a girls weekend and had a great time. The house and amenities were just as advertised, and the porch and backyard were the perfect spot to spend time together. Quiet and peaceful neighborhood. Andrew was a fantastic host - friendly, responsive, professional, and he provided a great guide of local recs and house instructions. The location was great for exploring Woods Hole and Falmouth by car. I would recommend!

We loved our stay here! Spent the weekend with our two young children and the house had everything we could need and more. It was walking distance to the beach and near great restaurants. Victoria also provided a list of local recommendations which we took a few of and loved them all! Would recommend staying here.

The house and Tam were fantastic! Tam's attention to detail in both the house and how it was prepared for us made it super easy and stress-free to get settled. We had an amazing time!