Kid-friendly holiday rentals in Chilmark

Very clean house. We loved the close location to the beach, because we had perfect weather all weekend. Quiet neighborhood, with large fenced-in backyard.

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.

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

Highly recommend Craig’s place in Sandwich! Lovely home, looked exactly as pictured and was immaculately clean and cozy. Craig was extremely responsive and friendly, would definitely stay here again! :)

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!

This little beach oasis is such a great value! We thoroughly enjoyed our stay here. As mentioned in the description, Patty & Bruce's spot is legitimately only a few minute walk from multiple beaches and is in such a cute little neighborhood! They have plenty of beach items should you not bring your own, which is great. The space itself is perfect for a quick little weekend getaway.

Great weekend at Susan's place. Susan met us with the key when we arrived and gave us a quick orientation and some great recommendations for local restaurants. The house was clean, had everything we needed, and the interior wood and many windows gave it a warm, bright feel. The neighborhood was very quiet. If you don't have a car, it is about a mile walk to downtown Oak Bluffs, which we enjoyed. The back patio among the trees and outdoor shower were additional pluses. We would definitely return and hope we get a chance to do so!

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!

Brian was very accommodating with a last-minute booking. Unfortunately, we had a miscommunication with another rental location and found ourselves on the island without a spot to stay. Brian was very responsive and got us into this cute apartment without any delay and saved our vacation. We were very lucky to find such a centrally located and well-cared-for apartment on such short notice.

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.

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. 🥰

The apartment was extremely warm and cozy and had the best home charm with all the books, making you feel right at home.

We enjoyed our stay at Monica & TJ's AirBnB and we were very impressed walking into a comfortable, modern welcoming home with everything we could ever need for our three week stay here. We appreciated the extra little things they would bring or do for us and we felt welcomed and safe during our long stay. We were here for a time being until we found a permanent residence but, we would certainly come back to stay for a vacation to enjoy the beautiful location by the water.

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!

Sharon’s accommodations were lovely- exactly what our family needed! The place was very clean and helped us feel at home while we were away! The location was very walkable and parking was easily found being the off season on the island. Will definitely stay again!

Between our visits in New York and Boston we stayed a couple of nights in Hyannis, Cape Cod. Perfect location for us on Main Street with restaurants, local shopping and close to the harbour. The apartment was bigger than expected. The host was helpful in giving advice of what to do, and we enjoyed a magic dinner at Anejo. We must come back!

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

Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.

To say the least this unit is better than advertised... Location, Location Location! Super clean, comfy beds, great parking...just easy!!...especially if you come in on the OB Ferry. Super convenient to all towns, but Oak Bluffs has everything and more to offer... Beach out front, super stores, excellent restaurants... We liked the Lucky Cat for dinner, Allai's for a quick hit/unique breakfast, The Overlook (maybe some of the best sushi ever!) for lunch and also dinner! Don't be overwhelmed by the waits... or the appearance of the crowds... they go fast! Heather is a spot on communicator and ready to help in any way. We look forward to a return trip!

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

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.

We were very happy with this comfortable 2 bedroom condo. Very clean and furnished nicely. Easy walk into town for shopping and dining. We had a few questions, which Leah answered quickly and in a friendly manner. Would stay again. Thank you Leah!

Alex's place was extremely clean and very well stocked with everything you need. It was a perfect place for family members to stay at. A convenience store is close by and Downtown New Bedford is a five minute drive. There is a school across the street and the neighborhood was fine. The beds and tv were great. Alex responded quickly if there were any questions. I would recommend this cozy place if you are coming to New Bedford.

Patrick is an amazing host and his place was so beautiful. Thank you!!