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

Kid Friendly Hotels in Pittsfield

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Check availability on Pittsfield Family friendly Hotels

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Pittsfield family-friendly hotels

A hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.

1. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
RM522
RM583 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

2. Hotel On North

Hotel On North
Pittsfield
RM547
RM612 total
includes taxes & fees
1 Nov - 2 Nov
Hotel On North
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 modern hotel with a large entrance, multiple floors, and a well-lit facade.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

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.
RM388
RM433 total
includes taxes & fees
19 Nov - 20 Nov
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 reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
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.

4. 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.
RM398
RM445 total
includes taxes & fees
15 Nov - 16 Nov
Best Western Plus Berkshire Hills Inn & Suites
A room with a pool table, arcade games, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
RM353
RM486 total
includes taxes & fees
12 Nov - 13 Nov
Berkshire Mountain Lodge
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A compact living space with a kitchenette, a dining area, and a sofa.
A bathroom with a toilet, shower, and bathtub.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
RM404
RM451 total
includes taxes & fees
25 Oct - 26 Oct
The Central Downtown 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 TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

7. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
RM290
RM324 total
includes taxes & fees
22 Oct - 23 Oct
FairBridge Inn Express
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

8. The Yankee Inn

The Yankee Inn
Lenox
  • Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
RM433
RM483 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A rectangular swimming pool with a white metal fence, surrounded by white lounge chairs and a blue umbrella.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A bathroom with a white sink, mirror, and toilet.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Family escape with outdoor pool and ski resort access—kids love the convenient location and amenities for all ages.
RM323
RM360 total
includes taxes & fees
25 Oct - 26 Oct
Howard Johnson by Wyndham Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Family memories made easy with an indoor pool, firepit, and cosy spaces just minutes from Bousquet Ski Area.
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
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

The Yankee Inn

The Yankee Inn

8/10 Good
"Efficient & comfortable. Very good value."
brian 1-night trip
Posted less than an hour ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is hands down my favorite hotel, and I have stayed here before and will keep coming back again and again! Everything about this place makes it feel special. The rooms are always spotless, incredibly spacious, and equipped with everything you need to feel right at home. Having a coffee maker, a full-size refrigerator, an oven, and a stove makes such a difference, especially for longer stays. The excellent jacuzzi is another big plus and makes it easy to relax and unwind. The property also has so many great amenities, and the surrounding nature is absolutely beautiful. There are plenty of amazing places to explore nearby, making it a perfect destination for a relaxing getaway while still having lots of things to do. What I love most is that the rooms feel more like a fully equipped apartment than a typical hotel room. It’s the kind of place where you can truly settle in, feel comfortable, and wish you could stay longer. I absolutely love this hotel, and it will always be one of my favorite places to stay. I will definitely be back again and again!"
Diana 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Great stay"
barbara 1-night trip
Posted 5 hours ago
Comfort Inn & Suites East Greenbush - Albany
Hotel On North

Hotel On North

10/10 Excellent
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 17 hours ago
Hotel On North
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Very clean room and apparently the room had been upgraded recently by real craftsmen. Well done. You don't expect this quality from an older motel, but the owners obviously take pride in the property."
Jeff 1-night trip
Posted 22 hours ago
Berkshire Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"Great location and reasonable price for the night/breakfast. Bedding was super comfortable and the handicapped bathroom was very nice. Although my original request to have the handicapped room (put in Sept 5th) was not passed on to the hotel, the desk clerk offered to make up a room for us if we were willing to wait 15 minutes. The parking lot was alright, but it is showing its age. The breakfast menu was alright; nice choice of fruits."
Debi 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"I liked the location and the restaurant was good"
Miguel 1-night trip
Posted 2 days ago
The Central Downtown Inn & Suites
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Nice people, ok and clean room. Too much light from around the window shades and all the gizmos (thermostat, TV etc.) to the point of inhibiting sleep."
Graydon 2-night trip
Posted 3 days ago
Hilton Garden Inn Lenox Pittsfield
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
Richard 1-night trip
Posted 6 days ago
FairBridge Inn Express

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.

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