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

Pittsfield Hotel Guide - Family Friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Family Friendly Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 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 buffet area with a counter, food items, and a beverage station.
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.
€106
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 cafe with a counter, seating area, and large windows.

2. 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.
€115
includes taxes & fees
20 Oct - 21 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

3. 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.
€103
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A dining area with wooden tables and chairs, a television, and a door with a sign.
A bathroom with a bathtub, a sink, and a mirror.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

4. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
€60
includes taxes & fees
27 Sept - 28 Sept
FairBridge Inn Express
A wooden deck with a table and chairs, surrounded by a white railing.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.
A two-story house with a balcony, a garage, and a driveway.
A living room with a sofa, a coffee table, and a television. There are curtains on the windows, and a lamp is on a side table.

5. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
€446
includes taxes & fees
17 Oct - 18 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A bunk bed room with a wooden floor, a ladder, a wardrobe, and a window with curtains.
A sign for The Hancock Village Inn in Berkshire, Massachusetts, with a rustic outdoor setting including a wooden bench, pumpkins, and a corn decoration.
A modern kitchen with wooden cabinets, a central island, a refrigerator, a sink, and pendant lighting.
A large white house with black shutters, surrounded by snow-covered trees and a fence.

6. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
€951
includes taxes & fees
23 Sept - 24 Sept
Hancock Village Inn Near Jiminy Peak
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside dock with kayaks and a covered boat ramp.
A dining area with large windows, wooden furniture, and a view of a lake.

7. 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.
€124
includes taxes & fees
29 Sept - 30 Sept
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.

8. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
€165
includes taxes & fees
18 Oct - 19 Oct
Element by Marriott Lenox Berkshires
An outdoor patio area with multiple chairs and tables, surrounded by lush greenery and trees.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.
A hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.

9. Cozy Corner Motel

Cozy Corner Motel
Williamstown
€90
includes taxes & fees
23 Sept - 24 Sept
Cozy Corner Motel
A room with a foosball table, arcade games, and a large dartboard.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A building with a porch and multiple windows, surrounded by purple flowers.

10. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
€131
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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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 4 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Great room and security. Like the breakfast setup . Staff is very good!"
Marian 2-night trip
Posted 6 hours ago
Quality Inn Great Barrington
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 22 hours 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 1 day 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 1 day ago
The Red Lion Inn
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Good"
Michael 1-night trip
Posted 2 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 8 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.