Kid-friendly holiday rentals in Chilmark

Great place felt right at home!!! Perfect for a nice relaxing getaway from the main city!

Madison has been an exemplary host, and the house was a great fit for 6 adults and 4 kids aged 4, 3, 1 and below 1. Even though we came for only a few days, I had lots of questions. Madison always responded promptly and helpfully. The host went beyond the call of duty by checking with cleaners when house became available, and facilitating an earlier check-in. That was greatly appreciated by our party. The house layout with bedrooms on two floors was perfect for us, where some kids who wake up real early slept on one floor, and others who wake up later are on another floor. Huge dinner table that could fit us all. Lack of clutter that let the energetic kids move around freely. Three bathrooms conveniently located, one on each floor. The availability of good quality, foldable beach chairs and a beach umbrella were a huge plus. The location of the house is in a quiet neighborhood, where we enjoyed walking, jogging or pushing strollers.

Alena's place had everything we needed for a lovely week on the Cape. Great pool and location between Mayflower and Dennis Village. My daughter loved the home's bright airy playroom and it kept us sane and entertained on a couple of rainy days. Would definitely visit again!

This was a family Christmas getaway, and it was perfect.

This place was everything we could’ve wanted for a week at the Cape. It’s in one of the best areas we have ever stayed on Cape Cod. We loved how they have the house decorated it was perfect. We had PLENTY of room for my wife, our two kids and me to relax when we were spent from activities. The yard was huge and there was wildlife all around. Nice and private location but 5-10 minute drive to get to anything you want. They were super accommodating to our last minute schedule shift and very responsive and give spot on recommendations on some things to check out. We would hands down stay again.

We had a fantastic family vacation in Falmouth and Anne’s house greatly exceeded all of our expectations! Comfortable, beautiful decorated and appointed with every amenity. We will be back!

Very quiet spot. Felt comfortable staying here. very good communication, very welcoming. Thank You Craig

We had a great Thanksgiving visit in a wonderful setting. The house is equipped with everything you could possibly need. The space worked very well for our family and the beds were comfortable. Jess provided us with all the information we needed for a great stay!

Cathleen made our one night stay easy and comfortable. The place was easy to find and nice and warm when we arrived. Streaming services on TV and lots of linens and cooking equipment as promised.

Great apartment. Close to the beach and great restaurants, but also quiet and peaceful. Slept better here than I do at home.

My husband and I throughly enjoyed our stay! Beautiful quiet home. Restaurant recommendations were very helpful! would recommend this place to anyone looking to visit the area!

Great home for our superintendent to stay in while working on a project. Highly recommend!

Nice place to stay. Easy to find and was quiet and had all the essentials.

We loved our stay at Michael's and Kara's beautiful house. It was so comfortable, clean and had everything we could possible want. We wished we could have stayed longer. Michael and Kara are so friendly and welcoming. They have this sunroom that is so very comfy. We will be back.

I had an incredible experience staying at Monica and TJ’s place! From the moment I arrived, everything was seamless. The check-in process was smooth, and the home was exactly as described—clean, cozy, and beautifully decorated. The location was perfect, making it easy to explore the area. The host was incredibly accommodating and responsive, ensuring I had everything I needed throughout my stay. The little touches, like [mention any standout amenities, e.g., complimentary snacks, extra towels, a well-stocked kitchen], made the experience even better. I would highly recommend this Airbnb to anyone looking for a comfortable and enjoyable stay. I’ll definitely be booking again in the future!

Mary Alice's place is so charming, equipped with everything I needed in daily life, and surrounded by full of green and peaceful neighbors. She is also very responsive and supportive in the communication. Definetely recommend, and wish to come back again!

Place was amazing and spacious. To bad we didn't have more time to enjoy it.

We had a wonderful time staying at the condo. Walkable distance to the beach and nearby shops. Great hosts and very helpful with the recommendations. We are considering to come back and recomend it to our friends.

Brian is a truly excellent host and his places are consistently great. I will always book with him if his properties are available!

Heathers condo was great and so close to ocean / beach. Would love to stay again during the summer to enjoy all it has to offer.

What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.

The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.

We stayed at this Airbnb for a weekend while visiting and attending a couple of family functions. The place was very clean and neat. The check-in was very clear and easy to access. Overall, good stay!!

Great location and a nice quaint spot for one or two ! Great value for the area as well