Book Kid-Friendly Hotels in Chatham from $261

Name: Chatham 3 Bedroom/2 Bath Retreat
Rating: 9

Find & compare hotels, resorts and vacation rentals for the whole family

Top Chatham Kid Friendly Hotels

Pleasant Bay Village Resort

1191 Orleans Road Chatham MA

$357 nightly

$408 total

Aug 12 - Aug 13

Total with taxes and fees

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, ...

9.6/10 Exceptional! (323 reviews)

"We had a wonderful stay! Everything was perfect! Definitely hope to come back!"

Reviewed on Jul 29, 2026

The Hawthorne

196 Shore Rd Chatham MA

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

9.4/10 Exceptional! (197 reviews)

"What a gem within walking distance of Chatham center. Directly diagonal from the famous Chatham Bars Inn but about half the price and a gorgeous water view. Ask for a room upstairs as the ones on the top level with the open lawn area all have great views. The staff were super helpful with recommendations ..."

Reviewed on Jul 27, 2026

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The Chatham Motel

1487 Main Street Chatham MA

A seasonal outdoor pool, free self parking, and free newspapers are featured at this motel. WiFi in public areas is free. A garden, a picnic area, and express ...

9.2/10 Wonderful! (635 reviews)

"Its very clean and the staff is nice. Its quiet place and the parking is by your front door i like that its easy to unload and load your stuff. I will definetly going back too stay again.."

Reviewed on Aug 3, 2026

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Chatham 3 Bedroom/2 Bath Retreat

Chatham MA

This vacation home features a garden, laundry facilities, and barbecue grills.

9/10 Wonderful! (53 reviews)

"Excellent location. Spacious house and the extra bonus room off the kitchen was perfect for my teenage daughters to set up camp. The back porch is comfortable, nice for an evening dinner at home. Abundant parking."

Reviewed on Jul 28, 2026

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Chatham Bars Inn

297 Shore Rd Chatham MA

$727 nightly

$832 total

Sep 3 - Sep 4

Total with taxes and fees

A private beach, a full-service spa, and 3 outdoor tennis courts are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool ...

Greyfinch Chatham Inn

946 Main Street (Rte 28) Chatham MA

$256 nightly

$293 total

Sep 1 - Sep 2

Total with taxes and fees

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area and luggage storage are also ...

Old Harbor Inn

22 Old Harbor Rd. Chatham MA

$599 nightly

$686 total

Aug 5 - Aug 6

Total with taxes and fees

A gym, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like buffet breakfast and WiFi in public ...

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels With Pools in Chatham

Captain's House Inn

369 Old Harbor Road Chatham MA

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9.8/10 Exceptional! (244 reviews)

Hotels with Childcare in Chatham

Pleasant Bay Village Resort

1191 Orleans Road Chatham MA

$357 nightly

$408 total

Aug 12 - Aug 13

Total with taxes and fees

9.6/10 Exceptional! (323 reviews)

Chatham Kid-Friendly Hotels

It’s not a family vacation if you can’t bring the entire clan with you, is it? Next time you have a few days off from work, plan a family-friendly getaway. Set off on an adventure the entire family will love, and book your stay at one of the kid-friendly hotels in Chatham.

Your little ones are the most important thing in your life, so make sure they enjoy your accommodation as much as you do. From a kids-only room service menu (macaroni and cheese, anyone?) to special perks like in-room video game consoles, these lodgings provide a little something extra for the smaller members of your crew. The best family-friendly hotels in Chatham may even offer playgrounds and other activities to keep the kiddos busy. What’s more, some hotels provide a babysitting service so you can get a few hours to yourself!

Whether you’re traveling with one small child or hauling around your entire extended family, Travelocity is here to help. Let us hook you up with hotels for kids in Chatham that will keep your youngsters happy without breaking the bank. You can save even more when you bundle your flight and hotel together, so what are you waiting for? Grab your family and get ready to explore!

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Recent Chatham Hotel Reviews By Fellow Wanderers

Uncommoner Hotel by Reverie Boutique Collection

5 out of 5

Posted 6 hours ago

Travelocity Verified Review

"Very impressed with the grounds and vibe of the hotel."

A verified traveler stayed at Uncommoner Hotel by Reverie Boutique Collection

Bayside Resort Hotel

4 out of 5

Posted 1 day ago

Travelocity Verified Review

"Pros of the hotel - great breakfast! Lots of choice, serve yourself. Indoor and outdoor pools great, towels provided (not on information but good to know). Firepit great, bar great. Cons - room a little dated but comfortable. Cleaner didn’t come for 2 of our mornings (3 including checkout day), only came on the first of the 4 nights, meaning we had damp towels and unchanged bins for the rest of the stay. Having missed us day 2 I made a point to ask the cleaner for it to be cleaned on the way to breakfast on day 3 and she still didn’t clean it. I even emptied the bin myself and walked it to her trolley after breakfast. It was a bit unbelievable. That said I would stay again, if the price was reasonable - it was tidy and breakfast was good and the pools were great. I didn’t love the area it was in itself, you drive to everything, but that said it’s in a convenient position on the Cape to get to places. On checkout the staff didn’t ask how the stay was, or speak at all to us really, so I didn’t say anything about the cleaner on checkout."

A verified traveler stayed at Bayside Resort Hotel