Family-friendly holiday 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!

This place was spotless. It was bright and neat. Nice decorative touches. Nicole was clear on all instructions and was very communicative. The area is very quiet. It’s 15 from p town and downtown Welfleet. If felt like a home and not a rental

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.

We traveled to the cape for a youth soccer tournament and wanted to find a place with room for our family and dog. Daniel's cottage was perfect for our family of 4 - a nice cozy cottage with beach access, all the comforts of home, and a great location. Daniel was a great host - proactive friendly location and a clean house with everything we needed.

Comfortable and cozy stay for 2 and a pet. Great location, sunny and bright. A/C was super quiet and cold.

Stacey made our stay a success - clear easy instructions and responsive. She has a great place to stay clean and with all the amenities we required to make our trip a fun one - whether we cooked at home or went out. Thanks again!

We had a wonderful stay at Pam’s charming Barnstable apartment! The space was clean, cozy, and had everything we needed (& more!) for a relaxing visit. Pam was welcoming, helpful, & kind to us & our two huskies (one of which can be awfully chatty) :) It's not always easy to find pet-friendly places, and we’re so grateful for her kindness & hospitality. The pups had a blast exploring the fenced in yard & doggy door. The location was quiet and peaceful, yet still conveniently located to beaches, shops, & restaurants a short drive away. It was the perfect home base for exploring the Cape, and a great spot to unwind at the end of the day. We felt right at home & would absolutely stay here again. Highly recommend — especially for fellow dog lovers!

We stayed at this historic home in South Chatham for a week during the first week of June. Great library, cozy interiors and a beautiful yard at the back, this cabin is comfortable and complete with a full kitchen and laundry amenities for a longer stay. The backyard was a peaceful retreat with birds, bunnies and turkeys visiting, where our toddler daughter spent hours playing. While here, we spent a week exploring Cape Cod National Seashore and the lighthouses in and around the Cape. Historic Chatham Lighthouse and Lighthouse beach are within few minutes drive from this home and provide opportunities for quiet wildlife viewing. Also situated close to ferries that travel to Martha's Vineyard and Nantucket. Highly recommend staying at this cabin. We will visit again.

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.

This place was INCREDIBLE!! Marla and her family were so responsive and so welcoming!! This house was the cleanest I have ever stayed in. The furniture was so comfortable and cozy. I would HIGHLY recommend staying here! I hope to come back in the near future!! Thank you Marla and family for being such amazing hosts!!

We really enjoyed our stay! The house is very spacious and in the perfect location. We would definitely stay here 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

This was our second time staying at Paul’s home, and once again had a wonderful experience! Paul and Meredith are welcoming, kind, and friendly. The house is spacious, and has plenty of room for our family to enjoy a week together - relaxing, cooking and playing games. The views are beautiful, and we enjoyed lots of time bird watching and soaking it in. We enjoyed easy access to our favorite Cape restaurants and shopping. This home is perfect for a Cape getaway, and Paul is a fantastic host!

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!

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