Book Kid-Friendly Hotels in Pittsfield from $81

Name: The Central Downtown Inn & Suites
Price range: $127 total

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

$169 nightly

$189 total

Jun 10 - Jun 11

Total with 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 ...

9.6/10 Exceptional! (863 reviews)

"Hotels Amazing stay here"

Reviewed on May 29, 2026

Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield MA

Fully refundableReserve now, pay when you stay

$146 nightly

$163 total

Jun 14 - Jun 15

Total with 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! (681 reviews)

"Staff members were friendly and the room was clean."

Reviewed on Jun 8, 2026

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

Fully refundableReserve now, pay when you stay

$111 nightly

$124 total

Jun 10 - Jun 11

Total with 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 ...

8.6/10 Excellent! (1,001 reviews)

"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"

Reviewed on May 30, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Fully refundable

$121 nightly

$135 total

Jun 22 - Jun 23

Total with 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, free WiFi in public ...

8/10 Very Good! (1,003 reviews)

"The hotel is under construction. This was not mentioned when reservations made. The only available parking was down the street at the bank. The television channels did not come in had to call for assistance. Then tv continued to have issues. On the ceiling and the wall there was dark colored “something” ..."

Reviewed on Jun 7, 2026

Berkshire Inn

150 W Housatonic St Pittsfield MA

Fully refundableReserve now, pay when you stay

$79 nightly

$88 total

Jun 10 - Jun 11

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 is provided and the front desk is ...

7.8/10 Good! (859 reviews)

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Reviewed on May 26, 2026

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

Fully refundableReserve now, pay when you stay

$73 nightly

$81 total

Jun 23 - Jun 24

Total with 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 ...

5.4/10 (824 reviews)

"This place was very rundown extremely dirty everything smells like smoke. The room was 90 bucks so I was not expecting much but this was the worst hotel I have ever stayed in. Front door is locked you have to biz the door to get to the front desk."

Reviewed on Jun 7, 2026

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$114 nightly

$127 total

Jun 11 - Jun 12

Total with 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 ...

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

$146 nightly

$163 total

Jun 14 - Jun 15

Total with taxes and fees

9.2/10 Wonderful! (681 reviews)

Pittsfield 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 Pittsfield.

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 Pittsfield 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 Pittsfield 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!

Package deals, things to do & more in Pittsfield

Recent Pittsfield Hotel Reviews By Fellow Wanderers

Vacation Village in the Berkshires

5 out of 5

Posted 14 hours ago

Travelocity Verified Review

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent value for the money. Friendly staff. I got a one-bdrm condo for the price of a standard hotel. No grocery atores nearby some come with supplies if you plan to cook."

A verified traveler stayed at Vacation Village in the Berkshires

The Yankee Inn

5 out of 5

Posted 21 hours ago

Travelocity Verified Review

"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."

A verified traveler stayed at The Yankee Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

1 out of 5

Posted 2 days ago

Travelocity Verified Review

"The hotel is under construction. This was not mentioned when reservations made. The only available parking was down the street at the bank. The television channels did not come in had to call for assistance. Then tv continued to have issues. On the ceiling and the wall there was dark colored “something” mold? dust? GROSS! Not worth the price."

A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG