Pet-friendly vacation 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!

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.

This was a very nice house. Carolyn answered every time I reached out. The house was just like the photos. We had a great time and will definitely recommend this property. Thanks Carolyn for making my 50th birthday memorable. ❤️

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.

Lisa's place is so lovely. It is so peaceful and has a great view. Check in was super easy and everything was as expected. Lisa is a great communicator and we were easily able to get questions answered. When we had an issue (not related to our stay) Lisa was so helpful and kind. Highly recommend.

Absolutely LOVE staying at Anna’s home that she graciously shares! Her home is like coming to your favorite aunts house while she is out of town and you just get to chill out and enjoy the area!! Quiet and peaceful, yet close enough to what I’ll call the “mall area” that has everything usually around a mall. Definitely check out The Head Landing Country Store for their coffee and DELICIOUS home baked goodies!!!

Loretta’s house is very comfortable and at a quiet and convenient location.

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!

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.

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

Stayed here for our daughter grad from Brown. Backyard beautiful and 20 min from Brown . Brought our adult children ,dog and grandma . Accommodated us all Thank you

We had a lovely and peaceful stay for our honeymoon on Martha's Vineyard. Easy access by car to Edgartown and Oak Bluffs. Very clean and pretty place with lots of thoughtful touches!

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!

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

Linda was great. I was moving to the area and was scrambling closing on my house and moving into my new home in town. Both were crazy and made staying here place easy and convenient. Highly recommend Linda.

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

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.