Kid-friendly holiday rentals in Chilmark

We loved our stay here. It worked well for two groups. The view was amazing and we had a fair amount of wildlife visit us. Very walkable down to cure coffee shops and restaurants and also right off the bike path. Devon was a fantastic host and very accommodating! Would stay again!

While the weather did not cooperate (it rained the entire time) the cottage and views made up for the weather. From the table to the couch the views are wonderful. The cottage is very well stocked from towels and blankets to the kitchen. We did not need anything that wasn't supplied. The bathroom is small but functional. The shower might not work well for a larger person. The neighborhood is quiet and feels very safe and peaceful. We enjoyed our long weekend and would book this cottage again.

Amazing home. Fantastic location. Peaceful and relaxing. One of our favorite vacation stays ever. Never turned the tv on… unusual for me. Hosts really thought of everything and more. Highly recommend if you are visiting Cape COD. 5+ stars.

A great location to get around Martha's Vineyard. A short walk from Oak Bluffs and taxis are plentiful plus a free bus service. Corrina's place is lovely, spacious and relaxing with a great coffee machine. Didn't realise couch folded into a bed (my bad) and shared the bed with my son. Would definitely use it as a base of I was in Martha's Vineyard again.

House was very cozy. Nice quiet neighborhood. Beds were very comfortable. I would not hesitate to stay there again.

It was a beautiful, secluded peaceful place. Kari and her family were wonderful hostesses and made us feel very welcome. Everything we needed for every day use was provided. It is not close to town; however, Uber was very handy and we figured out the bus system. My advice if you can bring a vehicle, it would be more convenient. It was also a great place for our small furry family members. Gus and Nala loved it. The outdoor space was lovely and the view was great. I got some lovely sunset pictures. There was plenty of space for everyone to relax and feel at home. I highly recommend it.

Thank you Brian we enjoyed our stay. The home is beautiful and so many amenities. The rooms are large and everything was so neat and clean. The open floor plan allowed us to sit and watch TV as well as cook in that beautiful gourmet kitchen. We will be back!

Felicia's place was wonderful, well designed and felt very cozy. You pull right up to the front door that helps you avoid street parking on the narrow road. She prepared a lovely basket to welcome us to the home, with snacks and a bottle of prosecco to celebrate. I was very pleased with her communication and thoughtfulness; there is a ton of amenities in the home, a fully stocked kitchen and bathroom and lots of recommendations for things to do. A beautiful space and person.

The outdoor space of the accommodation is beautiful—very calm and peaceful. With the GPS and Cathleen’s directions, it was very easy to find the place. The house is very well equipped—from the kitchen and bathroom to the living room—and the bed is super comfortable. It’s definitely worth staying for more than just one night, which unfortunately wasn’t possible for us. Cathleen’s parents are incredibly kind and friendly. Highly recommended!

If I could give 100 stars I would!! Out of all the airbnbs I have stayed at Jennifer’s listing has outdone them all!! First of all, Jennifer was the most amazing host and treated us like family! Secondly, the house was spotless, not a speck could be found (and I am usually picky about cleanliness) — it was absolutely exceptional!!! I will definitely be coming back multiple times. Thank you Jennifer for hosting us!

Mark's place was exactly how it appeared in photos. Great, walkable location. Easy to get to restaurants on Main St. There's a place to rent bikes just across the street. The stay was comfortable, quiet, and exceeded expectations. Thank you again, Mark!

We had such a wonderful stay at Gerda's place. Great host! Gave a lot of suggestions on what to do. The apartment was very clean and beautifully decorated. I really liked the location being right on the Main St., but it can be a bit noisy in the morning with the coffee shop directly across the street. I highly recommend this place.

This was our second stay and there's a reason we came back! The space is cozy and comfortable - We especially appreciated the easy flexible check in and snacky snacks and coffee. Thank you Norm!

Monica & TJ’s listing is exactly as pictured and described. It is spotless and well appointed. The extra little touches such as quality shampoo, conditioner, shower gel (not Wally World brand), snacks, and of course the pastries upon check in- are so nice. These things tell me that they care about their guests and their experience. Great binder on the “How to use” + suggestions of things to do, restaurants, etc. Very helpful! The best part was how close to the beach this rental is! 100% would stay here again; experience to value ratio = A+ !

We had a lovely time at Mary Alice’s place. She was incredibly kind, helpful, and responsive before, during and after our stay. Even though we weren’t able to meet in person, she made sure we felt welcomed and had what we needed. She also offered flexible checkin/checkout which we didn’t end up needing, but it was nice to have as an option! The location is a quiet and cozy neighborhood that offered us privacy but was also walkable to the main street. Many thoughtful touches incorporated into the place - I can tell that she treats her home with so much love and care, and it shows! Would recommend!

This was our second time at this location and it was expectedly perfect, which was why we chose it for this second visit. Great, quiet, beautiful neighborhood and perfect accommodations for our short stay. Would also be perfect for a longer stay as well!

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

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.

We stayed off season, but still plenty to do and see. We loved it!

I had a wonderful stay! The space was clean, quiet, and very comfortable. Perfect for a good night’s sleep after spending the day out. I came to Dennis, MA to celebrate a friend’s birthday and used the space primarily for resting, and it was just what I needed. The heat worked well, and the check-in and check-out process was smooth and hassle-free. Overall, I really enjoyed my stay and would definitely return if I’m in the area again.

Alex’s place was a great stay to recharge and relax after the long days we had last week. I would highly recommended this place for anyone popping through New Bedford, or staying for a few days! The airbnb was spotless and quiet and clean. I will be renting here again when I need somewhere to stay when I’m back in New Bedford! Also very close to downtown all the coffee shops, and restaurants! Quiet neighborhood.

The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.

We had a great six nights here. The space is super cool, well appointed with comfty beds and super soft towels, and was squeeky clean! We enjoyed the roof deck, the views to the waterfront, and the fireplace--and had an exceptional meal at Cork, too! Our stay was a combination of a work trip plus time to explore New Bedford and the SouthCoast and the location was great for both. Having a dedicated parking space was great, too. We would happily return.