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!

This is such an amazing place to stay was very difficult for us to leave after such a peaceful weekend, its close to everything which makes it extra convenient. Everything was clean and neat, the house its really big and comfortable, the beds are comfortable, the water pressure its great, the lounge patio the grill… there was just very relaxing. Was a great experience hopefully we’ll be back!

Jason’s place was perfect, very clean and had everything you need. He was proactive and very helpful. Gave us great recommendations for things to do and food in the area. Would have loved to stay longer. Will definitely stay again next time we are in Newport.

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!

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

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.

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!

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

Kimberly was a fantastic host. Her home was beautiful and well-maintained. It fit our group of 6 well and had lots of amenities for our baby (pack n play, stroller, baby gates, high chair)! There were beach chairs, beach & bath towels, and linens available which was unique from other places nearby and very helpful as we flew in. The location was great with a couple of stores nearby, several beaches, and restaurants. Kimberly was very responsive and accommodating as we navigated our stay. It was a great first trip to Cape Cod & we’ll definitely stay here again. I’d recommend trying Grumpy’s which is within 5 minutes & checking out a whale watching tour!

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!

House was very clean and comfortable. Kathleen was very responsive to all my inquiries both prior to and during our stay. House was easy drive to shopping and dinning as well as the local ponds and beaches. Although we did not cook if u plan to prepare meals be aware kitchen has limited pots and pans for cooking. Also would have like to have a tea pot to boil water. Otherwise had everything we needed for a wonderful stay

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!

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!

Emily was so kind and responsive and the house was exactly as expected. The walk to the beach was lovely and doable with the toddlers thanks to the wagon provided. It was a quick drive into all things Falmouth and a great home base for us. The stand outs for everyone were how comfy the beds were and we were all obsessed with the outdoor shower. Loved all the thoughtful amenities, such as games and kids dinnerware. Overall very stylish and comfortable. Highly recommend.

Our family loved this retreat!!

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

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.

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.

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!

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.

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.

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.