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

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Check availability on Pittsfield Family-Friendly Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Pittsfield family-friendly hotels

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
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.

1. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
฿4,292
฿4,794 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
฿3,750
฿4,189 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.
฿3,457
฿3,861 total
includes taxes & fees
2 Nov - 3 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
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.
฿3,137
฿3,504 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Berkshire Hills Inn & Suites
Room
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A bathroom with a large mirror, a sink, and a towel rack.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

5. 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.
฿3,624
฿4,048 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A modern apartment with a living room, kitchenette, and dining area.
A compact living space with a kitchenette, a dining area, and a sofa.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
฿3,322
฿3,711 total
includes taxes & fees
7 Oct - 8 Oct
The Central Downtown Inn & Suites
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.

7. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
฿2,084
฿2,328 total
includes taxes & fees
6 Oct - 7 Oct
FairBridge Inn Express
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

8. 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.
฿2,651
฿2,961 total
includes taxes & fees
6 Oct - 7 Oct
Howard Johnson by Wyndham Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

9. 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.
฿4,215
฿4,709 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A playground with a slide and climbing structures, a pool, and a building with a large window and a sloped roof.
Indoor pool
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
฿2,894
฿3,601 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Th property was beautiful and amongst the nature. The entire family had a good time in the pool, hot tub and the other kids amenities. The EV charging onsite was a plus"
Arabinda 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"The staff were helpful and the room was clean. Overall the experience was good"
tuhin 1-night trip
Posted 11 hours ago
The Central Downtown Inn & Suites
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"24-7 coffee was great"
wayne 2-night trip
Posted 14 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Hotel On North

Hotel On North

8/10 Good
"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."
Robin 2-night trip
Posted 1 day ago
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 4 days ago
Best Western Plus Berkshire Hills Inn & Suites

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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