Family-friendly holiday rentals in Chilmark

We stayed here for a bachelorette party and the house exceeded our expectations. Sherri was responsive and quick to answer all of our questions before and during the stay.

Great stay! Place is in a quiet residential area, yet centrally located and easy to get places. Nice yard and hot tub was a plus (clean and good temp). We didn’t have a chance to use the fire pit, but outdoor furniture and sitting area was nice with space for everyone. House was very clean, beds comfortable. Host was very responsive. Would definitely stay again.

The Villa was amazing for my family of 6. We truly enjoyed our stay and created some really great memories. Nance was especially great and was always available to help. She has created a few binders with some great information to provide an insiders knowledge of your immediate surroundings but also the Cape as a whole. If you like to hike there is a great trail about 20 yards from the front door that leads you to Grey’s Beach and/or Bass Hole Boardwalk. We used the hot tub, which is brand new, just about every night to relax after a full day of Cape activities. What a wonderful place to spend a week and create lasting memories. Thanks Nance!

Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!

Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.

I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!

Our family stayed here after graduation and it was perfect

We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

It was our second time staying at Amanda’s beautiful cottage and we hope not the last! The space is adorable and very spacious for a couple or a couple plus a guest (which was the case on this visit). The garden is a wonderful oasis to hang out and have meals and we appreciated Amanda being flexible to allow us to bring a solo stove. The area is so rich with wildlife and Mashpee Neck and the causeway beach are the best. We had an amazing time and can’t wait to come back.

Beautiful, peaceful and serene. A place to completely recharge! For both the 2 legged and 4 legged!

Very pleasant. Kristen oferred earlier checkin and very late checkout which allowed us to enjoy some additional hours at the beach and kayaking

A beautiful home in a peaceful neighborhood. I loved hearing the birds sing in the morning! Lots to do within the home, and very short ride to the city. I would definitely recommend this home to anyone looking for a home vibe! Also, lots of art on display and plenty of books to read. Thank you for the hospitality!

Stayed here for 1 night while working on the island. What a beautiful set up and it is in a great location to walk to town. The place was very clean and Brian is super helpful should you need anything! Will be looking to book again next time we are on island.

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.

Absolutely LOVE staying at Anna’s home that she graciously shares! Her home is like coming to your favorite aunts house while she is out of town and you just get to chill out and enjoy the area!! Quiet and peaceful, yet close enough to what I’ll call the “mall area” that has everything usually around a mall. Definitely check out The Head Landing Country Store for their coffee and DELICIOUS home baked goodies!!!

Perfect location. Host was there to even be sure I got a spot right in front of the cottage because it was busy time around there. Very clean and in tip top shape. Will definitely book there again.

Perfect house for 8 guests (we had 10 guests one night, but they had to sleep on a pull out couch). The pool and hot tub in the backyard is awesome for a summer getaway. Tons of common space/living areas, wish we were able to use it more! Kitchen has everything you need. The layout is pretty unique and took a bit to get used to, but it added to the overall charm. I would definitely stay here again and recommend it for a long weekend (we were here for a wedding and made a weekend out of it) or if you’re looking for a getaway to the Cape for a week. Great location too!

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

This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!

We stayed in the tree house suite. It had a lovely deck surrounded by trees and a great view of the sky. Craig and Ginny are as friendly a couple you will ever meet--always quick to answer questions and offer some great suggestions, Craig even offered to drop us off at a few places. They were so kind they felt like old friends. The beach is beautiful and a five minute walk away--which is great because they charge 25 bucks to park. So do the easy walk, and Ginny will provide chairs, towels, and umbrellas. Hyannis itself is a great place to walk around with lots of shops and great restaurants. We also took a ferry to Nantucket which was delightful, as well. I would visit them again without question. Go. You won't be disappointed. Michael and Rebecca

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!

Lovely location and very clean. Good spot to travel qround island. Lambert Cove was beautiful at sunset. If you have a bad back you might want to bring a mattress pad.

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.

Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend