A historic building with classical architecture, a traffic light, and a yellow taxi.

Search Family-Friendly Hotels in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Family-Friendly Hotels

Tonight
23 Sept - 24 Sept
Tomorrow
24 Sept - 25 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Pittsfield family-friendly hotels

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A bathroom with a large mirror, a sink, and a towel rack.

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
₹10,444
₹11,666 total
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
₹10,112
₹11,295 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Berkshire Hills Inn & Suites
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
₹10,898
₹12,173 total
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A bathroom with a bathtub, a sink, and a mirror.
A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

4. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
₹5,936
₹6,631 total
includes taxes & fees
27 Sept - 28 Sept
FairBridge Inn Express
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.
A dining area with large windows, wooden furniture, and a view of a lake.

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
₹12,198
₹13,625 total
includes taxes & fees
30 Sept - 1 Oct
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

6. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
₹16,155
₹18,046 total
includes taxes & fees
1 Oct - 2 Oct
Element by Marriott Lenox Berkshires
A room with a foosball table, arcade games, and a large dartboard.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A building with a porch and multiple windows, surrounded by purple flowers.

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
₹11,184
₹14,362 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.
A hotel room with a bed, a desk, and two wall-mounted lamps.
A wooden deck with a table and chairs, overlooking a road with a sign for 'Holliday Lodge'.
A small, compact bathroom with a toilet, sink, and a mirror above it.

8. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
  • Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
₹6,625
₹7,400 total
includes taxes & fees
30 Sept - 1 Oct
Econo Lodge Lee - Great Barrington
View all properties

Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included
All-inclusive
4 stars
5 stars

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 20 hours ago
Vacation Village in the Berkshires
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"It was clean spacious and staff was very nice"
Mary 1-night trip
Posted 2 days ago
Comfort Inn & Suites East Greenbush - Albany
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
William 2-night trip
Posted 2 days ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 2 days ago
The Red Lion Inn
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Good"
Michael 1-night trip
Posted 3 days ago
Berkshire Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Nice place, would stay again"
kaitlyn 1-night trip
Posted 9 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What's Pittsfield like for family-friendly holidays?
If you've been thinking about a trip with your children, the historic destination of Pittsfield is a good choice. The cycling trails, entertainment and lake views are just some of the things that make this the perfect spot for family trips. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 25.7 mi (41.4 km) from the city centre.
What's the best family accommodation in Pittsfield?
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other good options for your family trip include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn & Suites Pittsfield-Berkshires by IHG.
When's the best time to book a family-friendly holiday in Pittsfield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do with your family in Pittsfield?
Colonial Theater, Bousquet Ski Area and Barrington Stage Company are interesting attractions that you and your family will enjoy exploring while you are staying in Pittsfield. Make sure that you have lots of time for activities such as Guido's Marketplace and Berkshire Athenaeum.
What's the best way for us to get around Pittsfield?
To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have very many public transport options to choose from, so consider renting a car to explore more.

Explore a world of travel with Expedia