Pet-friendly holiday rentals in Chilmark

10/10 stay!! The cottage sits on a beautiful pond. We came during a rainy weekend so we stayed mainly inside. We turned on the electric fireplace & put on a movie. It was so cozy. Once the rain let up, we went outside and used the outdoor fireplace! So peaceful. Everything else you’d need, you are only a short drive from a cvs & grocery store. Melissa is a great host. We really appreciate how quick she responded with any minor concern we had. We look forward to more future stays at the cottage!

Hthaiwon’s place is so beautiful and airy. I loved the mid century modern decor. The way the house sits it feels like you’re up in the trees, which I loved. So many birds to listen to in the mornings while enjoying the deck. The walk down to the beach is quick and easy and it felt like it was our own private beach! We loved our stay and would definitely come back.

Robert’s place provided us a nice peaceful escape for a long weekend getaway. His instructions were clear and recommendations were helpful, and his home is in a nice location, close by to all Falmouth has to offer.

Midori's place was perfect for us - quiet neighborhood, clean, and spacious. The privacy lock on the front door was a bit tricky - you need to have a coin handy to turn it, which we would not have had but Midori told us to bring one. Great place for a nice trip to Cape Cod!

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.

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!

This house was very clean and adorable. The hosts were very responsive. There was what i believed to be a significant issue on the part of airb&b. They had the wrong adress listed for the house. Again this was not the hosts fault. It was listed as a house in Plymouth but was actually in Bourne, which I was very upset about after driving around for an hour and literally alomost trying to get into a strangers house at night in the dark. Airb&b refused to do anything for me to make this right and blamed it on google maps which is laughable. So for the house and the hosts (residentually) I give 5 stars. For airb&b I give 0 stars.

Great place to stay! Very close to the grocery store and not too far from town. Everything was clean, spacious and clutter free. When we did encounter a problem, they were so quick to response and fix it right away. Weather and company made it even better!

We had a wonderful stay and enjoyed this sprawling home in the center of a golf course. The host was friendly and responsive and the home had all the amenities we wanted. The yard was great for the dogs to run, and the beach and Audubon were within walking distance. Highly recommend.

Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!

The place was so spacious for our group of friends for a weekend away! It was very well kept and we had an amazing stay!

My husband and I had a lovely stay in this listing over Memorial Day weekend. The home itself and particularly the view were even more beautiful than pictured. Elena is a fantastic host - flexible, accommodating, and always quick to respond to any request. The adorable town of Warren, which is a few minutes drive away, boasts countless restaurants, bars, art galleries, boutiques, and more. I could not more highly recommend this home for couples, families, or groups of friends looking for a fantastic waterfront getaway.

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!

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

Stayed for the weekend while here for a concert. The place was immaculate. Cozy and had everything necessary for a relaxing time. Close enough to Boston and the cape to explore both if time had permitted. Host was proactive and involved in making our stay excellent and they were quick with any questions we had. Would absolutely stay again.

I recently booked this lovely cottage on West Island in Massachusetts for a weekend getaway with my mother to celebrate her 80th birthday. From the moment we arrived, we felt welcomed and comfortable. The cottage was spotless, cozy, and thoughtfully equipped for a relaxing stay. Greg is a gracious and considerate host. He provided helpful suggestions for nearby walks and accessible ways to enjoy the beach—especially thoughtful given my mother's limited mobility. The surrounding area is peaceful and quiet, perfect for unwinding. The neighborhood is residential and the neighbors we encountered were friendly and kind. I wouldn’t hesitate to book this cottage again. It was a perfect setting for a special weekend.

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!

House was impeccably clean, with bathrooms and kitchen welcoming. The kitchen had everything one could need to cook and comfortably prepare meals. Overall, an excellent house - strongly recommended!

Lovely home in Acoaxet with great water views and an excellent host.

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

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!

Had a great stay here- it was a cozy & clean space. You can tell a lot of care and thought were put into designing the space, didn’t feel very small because of how efficient and organized it was. The backyard was beautiful! Our puppy had a great time playing and running around in the yard. Location was convenient for us as well- made the most of our long weekend with short drives to the local towns, and day trips to Provincetown and Martha’s Vineyard. Also appreciate the variety of snacks that were available- especially your choice of Girl Scout cookies! Would definitely recommend this spot to others.