Book Kid-Friendly Hotels in Chatham from $251

Name: Chatham 3 Bedroom/2 Bath Retreat
Address: Chatham
Price range: $906 total
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

$388 total

per night

Jul 28 - Jul 29

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! (275 reviews)

"Great stay at Pleasant Bay and would highly recommend it. Rooms were spacious and very clean. The grounds are really nice with a koi pond, gardens and lots of seating areas. Pool and hot tub area also really nice. Staff was very friendly and helpful. Shout out to Peter at the front desk, who was ..."

Reviewed on Jul 19, 2025

Old Harbor Inn

22 Old Harbor Rd., Chatham, MA

$525 total

per night

Aug 6 - Aug 7

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! (160 reviews)

"Very professional and well done b and b in capecod. Can’t recommend enough"

Reviewed on Jul 6, 2025

The Chatham Motel

1487 Main Street, Chatham, MA

$251 total

per night

Jul 24 - Jul 25

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! (614 reviews)

"Room was spacious and clean."

Reviewed on Jul 10, 2025

Chatham Bars Inn

297 Shore Rd, Chatham, MA

$1,064 total

per night

Jul 24 - Jul 25

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 ...

9.2/10 Wonderful! (775 reviews)

"Old school hotel complex in a great location overlooking the Sea. Great ambience in the main lodge & dining facilities. Very kid friendly with the main pool swarming with kids. At one point I noticed 8 small kids in the large jacuzzi at one time - unusual for a luxury property. The pool experience ..."

Reviewed on Jul 16, 2025

The Hawthorne

196 Shore Rd, Chatham, MA

$497 total

per night

Jul 28 - Jul 29

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! (183 reviews)

"I stayed there for a wedding. The staff was super helpful and really went above and beyond. The place was beautifully kept and had a charming vibe. I’d definitely recommend it!"

Reviewed on Jul 18, 2025

Greyfinch Chatham Inn

946 Main Street (Rte 28), Chatham, MA

$456 total

per night

Aug 17 - Aug 18

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! (229 reviews)

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

Travelers say...

"This place was cute, clean and in a very convenient location"

Reviewed on Jul 21, 2025

Chatham 3 Bedroom/2 Bath Retreat

Chatham

$906 total

per night

Aug 12 - Aug 13

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

8.8/10 Excellent! (42 reviews)

"Pam was an excellent host. The house is in a great location and served as a perfect home base for my group over 4th of July Weekend."

Reviewed on Jul 7, 2025

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

Get rates

9.8/10 Exceptional! (189 reviews)

Hotels with Childcare in Chatham

Pleasant Bay Village Resort

1191 Orleans Road, Chatham, MA

$388 total

per night

Jul 28 - Jul 29

9.6/10 Exceptional! (275 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 $251 per night. Our prices range up $1,064 per night if you want to enjoy the high life.

How many family-friendly hotels are there in Chatham?

With over 5,050 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.