Book Kid-Friendly Hotels in Chatham from $216

Name: Chatham 3 Bedroom/2 Bath Retreat
Address: Chatham
Rating: 8.8

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

$220 nightly

$252 total

Oct 23 - Oct 24

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! (299 reviews)

"The room and patio were beautiful. Comfortable bed. Parking spot right outside the room. Very quiet."

Reviewed on Oct 2, 2025

Old Harbor Inn

22 Old Harbor Rd., Chatham, MA

$269 nightly

$308 total

Oct 29 - Oct 30

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 ...

9.6/10 Exceptional! (161 reviews)

"The room was cozy and very clean. Service was friendly and welcoming. We fell in love with the whole Chatham area and had a great time!"

Reviewed on Oct 16, 2025

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! (630 reviews)

"Very safe . Cafe Mood great food run by Jamaican family"

Reviewed on Oct 11, 2025

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The Hawthorne

196 Shore Rd, Chatham, MA

$231 nightly

$264 total

Oct 23 - Oct 24

Total with taxes and fees

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.

9.2/10 Wonderful! (193 reviews)

"This place has a wonderful view of the bay and North Beach Island. It's got the charm and classic style of cape cod and perfect location for a stroll on the beach or walk into town or to light house beach."

Reviewed on Oct 6, 2025

Chatham Bars Inn

297 Shore Rd, Chatham, MA

$397 nightly

$455 total

Oct 30 - Oct 31

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 ...

9/10 Wonderful! (791 reviews)

"Excellent experience all around Gorgeous location and beautiful hotel Lively lobby"

Reviewed on Oct 13, 2025

Greyfinch Chatham Inn

946 Main Street (Rte 28), Chatham, MA

$189 nightly

$216 total

Oct 23 - Oct 24

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 ...

8.8/10 Excellent! (249 reviews)

Families like: Outdoor pool, close to beach, bicycle rentals

Travelers say...

"Nice place"

Reviewed on Oct 12, 2025

Chatham 3 Bedroom/2 Bath Retreat

Chatham

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

8.8/10 Excellent! (47 reviews)

"House listing was on point. Bedrooms and living area a good size. We had 5 adults staying there and we were not tripping over each other. Communication was awesome both before and during our stay. House is in a very quiet area. Cleaning crew could have done a better job clearing out the previous ..."

Reviewed on Aug 29, 2025

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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

Pleasant Bay Village Resort

1191 Orleans Road, Chatham, MA

$220 nightly

$252 total

Oct 23 - Oct 24

Total with taxes and fees

9.6/10 Exceptional! (299 reviews)

Hotels with Childcare in Chatham

Pleasant Bay Village Resort

1191 Orleans Road, Chatham, MA

$220 nightly

$252 total

Oct 23 - Oct 24

Total with taxes and fees

9.6/10 Exceptional! (299 reviews)

Book a stay at the best kid-friendly hotels in Chatham

How much does it cost to stay in a family hotel in Chatham?

You can book a stay at a kid-friendly resort in Chatham from just $216 per night. Our prices range up $455 per night if you want to enjoy the high life.

How many family-friendly hotels are there in Chatham?

With over 4,596 hotels in Chatham, you have a great selection of kid-friendly places to stay. Whether you’re looking for a cheap-and-cheerful property with plenty of space or an activity-filled kid-friendly resort, there’s a getaway to suit your style and your budget at Travelocity.

What is Travelocity’s cancellation policy for family hotels in Chatham?

We offer free cancellation on select hotels. Policies can vary per property so it's best to check before you book. If you need to amend or cancel your vacation, just visit our Customer Service Portal. 

What are the best kid-friendly hotels in Chatham?

At Travelocity, you can book the best family-friendly Chatham hotel for you and your family by filtering your search by price, property type, and a range of amenities such as breakfast included or free airport shuttle. Use the map to see where the hotels are and the attractions they’re near.

What should I expect in the family-friendly hotels in Chatham?

When you book a kid-friendly Chatham resort, you can expect fun for all the family. Think pools, waterparks, and hot tubs. Think babysitting, kids’ menus, games rooms, and sport facilities—discover your ideal family vacation. Many resorts keep the kids happy, so you can indulge in bars, restaurants, and spas. Check details for each property as offers may vary.

How can I find family hotel deals in Chatham?

Just enter your travel dates and sort your results by price. You can even filter your results by budget, so you’ll only see the deals that are right for your pocket. It’s easy to find great deals on family-friendly hotels in Chatham with Travelocity. 

When is the cheapest time to go to Chatham with your family?

The cheapest time to visit Chatham is usually .

When is the best time to go to Chatham with your kids?

The most popular months are and are great for booking in at a Chatham kid-friendly resort. If you want a quieter vacation—or the kids aren’t in school yet— are usually less busy, but you can find incredible deals all year round with Travelocity. 

Why book a Chatham child-friendly hotel with Travelocity?

Because we search the entire market, so you don’t have to. You’ll find great deals on everything from weekend trips to two-week family vacations. Whatever your budget or your wish list, we’ve got what you’re looking for.