Book Kid-Friendly Hotels in Pittsfield from $78

Name: Holiday Inn & Suites Pittsfield-Berkshires by IHG
Price range: $144 total
Rating: 7.8

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

Top Pittsfield Kid Friendly Hotels

Hotel On North

297 North Street, Pittsfield, MA

Fully refundableReserve now, pay when you stay

$189 nightly

$211 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's ...

9.4/10 Exceptional! (745 reviews)

"Staff were excellent and welcoming."

Reviewed on Jul 21, 2025

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield, MA

Fully refundableReserve now, pay when you stay

$195 nightly

$217 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A terrace, ...

9.2/10 Wonderful! (636 reviews)

"Our room was very comfortable and quiet so that was good. It is not in a very scenic location, but that seems to be typical in this area. It is on the highway overlooking some other businesses but there is a very popular food market there close by which is nice."

Reviewed on Jul 12, 2025

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

$129 nightly

$144 total

Jul 27 - Jul 28

Total includes taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on ...

8.6/10 Excellent! (299 reviews)

"Nice kitchen, a comfy couch, and clean space. Bathroom is small and toilet needed two flushes. Location is great, right in downtown Pittsfield. We appreciated the service since they brought us extra towels minutes after we asked."

Reviewed on Jul 16, 2025

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Fully refundableReserve now, pay when you stay

$127 nightly

$141 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the ...

8.4/10 Very Good! (1,011 reviews)

"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on Jul 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

Fully refundable

$129 nightly

$144 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...

7.8/10 Good! (827 reviews)

"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield."

Reviewed on Jul 21, 2025

Berkshire Inn

150 W Housatonic St, Pittsfield, MA

Fully refundableReserve now, pay when you stay

$86 nightly

$97 total

Jul 31 - Aug 1

Total includes 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 is provided and the front desk is ...

7.6/10 Good! (782 reviews)

"It was clean and recently refurbished. The pool was a nice relaxing asset after a long day. The continental breakfast was just coffee or tea."

Reviewed on Jul 22, 2025

FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA

Fully refundableReserve now, pay when you stay

$69 nightly

$78 total

Aug 20 - Aug 21

Total includes taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front ...

5.2/10 (749 reviews)

"Shampoo and toilet paper should have been In the room."

Reviewed on Jun 29, 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 Pittsfield

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield, MA

$195 nightly

$217 total

Jul 27 - Jul 28

Total includes taxes and fees

9.2/10 Wonderful! (636 reviews)

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

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

You can book a stay at a kid-friendly resort in Pittsfield from just $78 per night. Our prices range up $217 per night if you want to enjoy the high life.

How many family-friendly hotels are there in Pittsfield?

With over 1,367 hotels in Pittsfield, 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 Pittsfield?

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 Pittsfield?

At Travelocity, you can book the best family-friendly Pittsfield 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 Pittsfield?

When you book a kid-friendly Pittsfield 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 Pittsfield?

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 Pittsfield with Travelocity. 

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

The cheapest time to visit Pittsfield is usually .

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

The most popular months are and are great for booking in at a Pittsfield 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 Pittsfield 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.

Package deals, things to do & more in Pittsfield

Recent Pittsfield Hotel Reviews By Fellow Wanderers

Berkshire Inn

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"It was clean and recently refurbished. The pool was a nice relaxing asset after a long day. The continental breakfast was just coffee or tea. "

A verified traveler stayed at Berkshire Inn

Best Western Plus Berkshire Hills Inn & Suites

5 out of 5

Posted 6 days ago

Travelocity Verified Review

"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites