Kid-friendly holiday rentals in Chatham

You won't find more responsive hosts - literally within minutes. Check-in and communication throughout was great. And it's the first rental I've ever seen that had REAL toilet paper! IYKYK! They were super clear about everything. The only small issue we had was with the AC. It's listed as Central AC, which it has but only on one floor. This wasn't a big deal because it was later in the season but if it was in the middle of the summer it would have been an issue. The first floor didn't get any of the AC and just cracking the door from the upstairs wasn't really sufficient to cool it down, even at night. Again, not a problem around Labor Day when we were there but in mid-July I don't think it would have been very comfortable to sleep there. But other than that, a great stay in a great location.

Perfect little cottage off the beaten path but central to everything Cape Cod. We took lots of little day trips and relaxed in the cottage in the evening. Downtown Chatham is adorable and lots of great places to eat! We took a ferry to Nantucket one day and the dock was only 5 minutes away, free parking - so easy. Jonathan was quick to respond with any questions we had. The cottage had a full kitchen so we were able to cook our breakfasts at home and pack our lunches for the beaches. Even on the rainy days we didn't have to go far to find cute coffee shops and shopping. We didn't spend much time on the beach close to the cottage but did go down there one evening to watch the sunset. Right down the street!

We loved staying at Paula’s home! It immediately feels warm and cozy. The furniture looks nice and is comfortable as well. It is well stocked with kitchen utensils and toiletries. They left specific instructions and local recommendations. The home is tucked away from the road which makes it feel like a beautiful private getaway. As a book lover, I was thrilled to find some reading options too! We would definitely recommend staying in this lovely home.

We had a wonderful long weekend stay at Patrick’s place in South Chatham! The home was exactly as described—clean, modern, and incredibly well-equipped with everything we needed and more. The thoughtful amenities made us feel right at home. The location was perfect: close to downtown Chatham and right on the bike path, which made exploring the area super easy. We couldn’t have asked for a better spot for a relaxing getaway. Would absolutely stay here again!

We had a great time staying at this Airbnb! If I find myself returning to Cape Cod I will be sure to look if this house is available again.

This stay in Chatham was lovely. The house was adorable and had plenty of space for all of us staying that weekend. The house was thoughtfully designed with everything you need. You will have to either bring your own towels and sheets or rent and you will need to clean everything to be “broom” clean, which does offload more work and costs onto guests, but otherwise everything was fantastic. The location is so close to everything and is just beautiful.

The Happy Yellow House was all I hoped for and more. Clean and well equipped, and very comfortable. The location couldn't be beat! Right down the street from a beautiful Nantucket sound beach and close to the amenities of Chatham. The house is in a quiet neighborhood of summer homes and was very peaceful. Caitlin is a superb host and responded promptly when there was a little snafu with a faulty smoke detector (at 10pm!), offering to have an electrician out on an emergency basis. (The electrician had just serviced the smoke detectors. As Host, Caitlin couldn't have been more pro-active or responsive) Luckily, I was able to solve the problem by simply removing and replacing the batteries. I would not hesitate to book this rental again.

Absolutely adorable! Would stay here again! Be sure to read the details when you get there (my fault I learned you can’t take 2 hot showers back to back…they do tell you that but I missed it). Great location. Perfect crash pad for a weekend as wedding guests!

this was a great place to stay in brewster. it is across the street from my favorite coffee shop and walkable to several great restaurants in the area. ann was a great host and easy to talk to. i definitely recommend staying here!

Such a lovely place! Peaceful, super clean, and overall excellence! Best Airbnb experience I've had so far!

Diana and Greg's place is a wonderful place to stay, brimming with nature, quaint and comfortable living space and wonderful hosts. A nice walk to the beach, enjoyed the birds and frog sounds were the highlights and Orleans allows the entire Cape Cod to be accessible under an hour drive. An awesome weekend adventure and appreciate Diana and Greg opening up their doors! Cheers!

Had a great stay in Chatham at this Airbnb. Heather the host was extremely friendly and made us feel very welcome. The place was very well located in Chatham, well appointed and comfortable. We were very happy with our stay there, including a pack and play for our 16 month old. Would highly recommend a stay here to anyone.

My fiancé, dog Bandit, and I stayed here for a few days and it was comfortable & had everything we needed. The private beach was a 10/10. Perfect place to watch the sunrise and there are gray seals constantly swimming by near the shore, so cool!! Make sure you take a look at the ideas and recommendations that Patty left in the blue ring binder. I recommend the Rock Harbor Grill for dinner & Ice Cream Cafe for dessert. Close by to the awesome rail trail for dog walks and only a 50ish minute drive to the tip of the Cape Cod National Seashore. I will say BEWARE of ticks if you’re walking your dog. They are plentiful in Cape Cod, believe it or not. Finally, Patty was a wonderful host. We would definitely choose this Airbnb when visiting Cape Cod again.

I got this Airbnb for the weekend because I was proposing to my girlfriend in a Hyannis dinner train. This was the only spot that looked private and worthy of an “engagement weekend getaway” vibe as opposed to hotels and other Airbnbs. Meagan even allowed a friend of mine to show up and decorate the apartment with “Just Engaged” signs and fake candles and fake rose petals, which made the bedroom look even more romantic. My now-fiancé could not express enough how much she loved the place. Quiet, safe neighborhood, good eating spots less than 10 mins away in car, great water pressure, everything you could ask for. If we’re going to be knit-picky, the only thing we can complain about was that the A/C did not seem to work. The wall unit was open like if it was working, but no air was coming out of it. I forgot to mention this to Meagan during our stay, as I’m sure she would have rushed to help us. We slept with the windows slightly open and it was just as nice.

Lisa’s place is perfect and just what we needed. Very clean and got everything you need, close to so many beautiful spots and lots of dining options in the area. I’ll miss Lisa’s beautiful property and serene nature backyard. Thank you

This is my third time staying at this quaint place! Great location, quiet, and everything you need for a couple!

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.

It is the most well equipped rental we have ever stayed in, all furniture very comfortable and convenient. We would definitely recommend

Anna’s place was exactly what we needed to have a peaceful and relaxing Memorial Day weekend stay. We knew the weather might be on the cooler side, so purposefully wanted to stay where there was the possibility of using the indoor pool – the sponsored guest passes were a huge benefit here, and Oceans Edge staff even went above and beyond, adding an extra day to our pool access since we were picking them up so late in the day. The condo was clean and filled with all the essentials, in a very quiet area of the property. Would definitely stay again!

Alan's place was a perfect home base for our Provincetown getaway. Checking in/out was a breeze, we found the condo clean and lovely and the location cannot be beat. We would definitely stay here again - thank you!

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.

We really enjoyed our stay. Great condition, really clean, easy parking, and great location right at the Ocean Edge resort. Rob was an excellent host, super communicative and responsive. Would stay again!

We had a great stay. We really appreciated that they let us check in a little early too! The views and easy access to the beach were perfection and we really loved the deck space. The living room windows gave beautiful views. Very walkable and easy to navigate. Definitely will be keeping this gem on our radar for our next trip to Provincetown.

Courtney was an amazing host! Her place was beautiful and clean. I would definitely stay again! Check this place out it’s perfect!