Family-friendly vacation rentals in Chatham

The Penny's House is close to all the beaches, great restaurants and the bike path is accessible via the back of the property which we loved. Her house is beautiful and the kitchen was fully stocked with all cookware you needed to make family dinners together. My family was very comfortable with out stay here! Thanks, Kathleen,Jack and family

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.

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!

Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.

This house had such an exceptional energy to it, it was so peaceful. The hosts are unbelievably welcoming and helpful! You can quickly tell how remarkable this place is. It was such a pleasure to stay in this house and explore the island this weekend. It was our first time on MV and it was wonderful. The beach was so close and relaxing, and amazing restaurants a just a short walk down the street! A huge thank you to the hosts for allowing us to stay in their beautiful home, it was just what we needed for a relaxing weekend.

We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!

Beautiful home! David gave perfect instructions for everything about the house and was very responsive. We all had a fantastic weekend, and will definitely be booking again! Thank you David!

We loved our weekend at Karen's place! The house was cozy and clean, and had everything we needed for a comfortable stay (including treats for our pup)! The yard and deck were nice and private, and the house was conveniently located to many restaurants, shops, and not far from the water. Karen made us feel right at home!

We attended a wedding at the Ocean Edge Resort and we found Paige's home to be convenient to the venue and activities and a great alternative to staying on property. The home was clean and neat and had everything we needed. The weather turned out beautiful so we took full advantage of the outdoor space. I would highly recommend Paige's home to anyone who likes to be close to the beach, restaurants and golf, but far enough away to be quiet and peaceful.

Comfortable and cozy cottage to stay in. Bonnie was great at communicating, and the offer (didn't have to ask) to check in early was greatly appreciated. Even though the weather (Nor'easter) wasn't the best, the cottage was great. The gas fireplace was used and added to the warmth of the cottage. Little things that the cottage was stocked with was very helpful (dog bowls) even if weren't used. Just knowing the cottage has little details will have me renting again. Thank you!

Sue's place was perfect for our mother-daughter weekend. Sue provided a comprehensive list of restaurants in the area, but we prepared all of our meals in the kitchen, which was well-appointed, very much appreciated. We enjoyed daily walks to the beach. Though it was off-season and overcast, inside it was perfectly cozy. The fireplace was great to return to. Sue was quick to return texts, and very welcoming. The snack basket was well received! Would highly recommend.

We stayed at Rob's place for a few days for New Year's Eve and it was great. The house was very comfortable for a few couples to hang out, cook some meals and enjoy the beautiful views. At low tide you can walk from the house down to the marsh and follow some rough trails or walk a little further to Lt. Island for some sandy beach. The wood stove made it great winter haven, to sit by the fire and enjoy the views of the tides rolling in and out. The architecture of the house is also interesting and reminiscent of other Wellfleet modernist homes.

The cottage was beautiful and in a perfect location! We loved walking to the beach and the cottage’s close proximity to so many good cafes and restaurants. The house had everything we would need. Loved the backyard too and it was very clean and cozy!

The house is amazing! It has everything that you would need and is so comfortable. The property is peaceful, and it feels like you’re on your own little island while still being minutes from stores and restaurants. We had a perfect weekend celebrating some milestone birthdays in our family.

The property was beautiful, secluded, and quiet. Not far at all from fun things to do, by any means. The Apartment was spacious, clean, and has everything you need in case you forgot something. The hosts were respectful of your privacy, but if you needed anything, they were always there to help. I highly suggest a stay here.

Rob was a great host ! He responded within a timely manner and the place was very clean and felt just like home. I would suggest bringing board games and such for the rainy days. For the folks who enjoy cooking the kitchen was fully stocked with everything you need. I would also recommend renting bikes or taking an Uber if you don't like walking. The walk to town was about 25 minutes. Overall great stay would love you stay her again it gives you the peace and quiet while also being close enough to everything and a beautiful view of the ocean.

Great place. Very central to Main Street. Quiet, plenty of space, good parking, easy communication and check-in. We will come again!

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

Beautiful house, with quiet pond in the back. Most days had the whole pond to ourselves. Perfect spot for a weekend fish trip.

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!

We had a wonderful stay at Garrett’s place. The apartment location can’t be beat, right on the water and walking distance to town but also nice and peaceful. Our family enjoyed the balcony and the comfy living room and kitchen. Would recommend!

Patrick is a fantastic host and was very proactive and responsive when we ran into a problem outside anyone’s control. We would definitely recommend this home and host to others traveling to the area