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!

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

We have been going to this area for decades and decided to rent vs other options this year. Place very comfortable, easy access (bad leg) with deck ramp key. Water pressure fab as family actually commented. Would look to do again! Excellent…

Lovely stay! Would highly recommend to anyone staying in the area.

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

Zack’s house was beautiful and exactly as pictured. The lawn/outdoor area was even more beautiful than expected. He was very responsive and proactive, with detailed instructions for every part of the check in and check out process. The house was the perfect size and layout for our group, and was fully stocked with enough towels and amenities such as shampoo & conditioner in every bathroom. I absolutely would stay with Zack again, either at this house or any of his other properties.

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!

Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray

Our group of six adults had an amazing stay at this beautiful, modern home in Woods Hole! The house was impeccably designed and well-stocked with everything we needed for a comfortable stay. The beds were incredibly cozy, ensuring everyone got a great night’s sleep. The location was perfect—steps away from the island ferry, making our trips to Nantucket and Martha’s Vineyard a breeze without the hassle of parking or shuttles. We loved the private nooks throughout the house, ideal for curling up with a book and coffee. The grill was a highlight, allowing us to enjoy several evenings cooking together. Being within walking distance to fantastic restaurants in Woods Hole was a huge plus, adding convenience and variety to our dining options. This home exceeded our expectations, and we highly recommend it to anyone visiting the area!

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.

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!

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.

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

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 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!

Staying at Rebecca’s Hideaway was a wonderful experience! I stayed with the family during the Thanksgiving holiday during the offseason and the location was absolutely beautiful. The hosts went above and beyond to make us feel comfortable and even left us treats at the house! The location of the house was private, but a close enough drive into downtown Edgartown to get drinks and dinner or do some shopping. There are many options to relax outdoors and it’s a close walk to get to South Beach to enjoy nature. I would definitely recommend staying here and would rebook in a heart beat!

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

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.

Exceptional - believe the hype/countless 5-star reviews. Amy's home is an ideal home base on MV, especially for families. The location is great (easy walk to town), the backyard is gorgeous, the home itself is spotless and has every toy/amenity you could want. (We especially loved the proximity to the large, well-maintained playground and town library.) Amy is an excellent host and made herself available before and during our stay. We can't wait to come back.

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!