Kid-friendly holiday rentals in Chilmark

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

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!

Home was very cute and met our needs. It snow while there and Craig messaged to see if we needed to be plowed out. They did an amazing job! The stay was great!

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!

We stayed at Gina’s for my bachelorette trip with my 6 friends and we LOVED it. It was exactly what I wanted which was a peaceful, fun, and wholesome getaway with great restaurants and shopping. The pool was beautiful and the screened in sun room/porch was the perfect hang out spot. Gina was extremely responsive and super friendly which I appreciated. The house truly felt like our little getaway and home for the weekend. I also thought that the house and specifically the living room space was bigger in person than it looked in the pictures which was great! We had so much fun and didn’t want to leave!! Highly recommend!

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.

We loved our stay and the next time we visit, we won't want to stay anywhere else! Lovely place! Lots of space, comfie beds, nice location. The hosts are wonderful and will make sure you have everything you need. 🥰

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!

Irina is easy to communicate with. The place is very clean, just as described. Comfortable and has everything you need for a short stay. Bathroom is very nice and clean. Location is very accessible to downtown by Uber, takes less than 10 min. Walking distance to downtown is about 1.5 miles and it is a safe and mostly paved walk. Area feels safe, a little loud as it is near the street and above the cafe but nothing that was really disturbing of sleep. Thank you!

I highly recommend Renee's for anyone wanting to explore downtown Hyannis/Barnstable. I stayed at Renee's for a 2 week work trip and it was the perfect location. Everything you might need is within a short walk; coffee, restaurants, grocery stores, and several gyms. I even enjoyed a short winter trip to the beach =) The apartment is up a steep flight of narrow stairs, so Id keep that in mind when considering how much to pack. Yes, you can hear the music from the restaurant below, but it wasn't bothersome to me because it wasn't too loud and I slept right through it. Ear plugs and sound machines are provided for lighter sleepers or anyone that might be bothered by a little background noise. The apartment was spotless and looks exactly as it does in the photos. Great location , super clean, and I definitely appreciated the washer & dryer for the longer stay.

The apartment was very clean, well stocked, and had plenty of privacy.

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.

Such a beautiful stay right next to the beach in a wonderful and walkable town! Jamie was an incredible and responsive host who came out to help us when the smoke detector was going off. She was happy to change the batteries for us and help out. The place was spacious for two people and offered everything we needed for a wonderful family vacation.

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

Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.

What a darling space! We felt right at home. It was quiet and cute inside and we were able to really relax. Thank you, Sam for such creating an inviting living area!

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.

Sam was a great host! He was very helpful and quite nice. The condo was a beautiful little place and looked exactly like the photos. Very clean and homey. I would absolutely stay here again!

Great location and so much nearby. We only stayed 2 nights as we flew in for a family party, but was perfect for what we needed. Great location, very clean and spacious, and easy self check in and out. We appreciate the host and will definitely stay again if we need to come back for anymore family functions.