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

Find Kid Friendly Hotels in Pittsfield from S$85

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Check availability on Pittsfield Family friendly Hotels

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Pittsfield family-friendly hotels

A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
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.

1. Hotel On North

Hotel On North
Pittsfield
S$144
includes taxes & fees
2 Nov - 3 Nov
Hotel On North
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 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.

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.
S$133
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Berkshire Hills Inn & Suites
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A hotel patio with outdoor seating and a fire pit.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A spacious living room with a large sofa, a coffee table, and a fireplace.

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
S$182
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern cafe with a counter, seating area, and large windows.

4. 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.
S$147
includes taxes & fees
5 Nov - 6 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Room
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.
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

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.
S$140
includes taxes & fees
7 Nov - 8 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A room with a pool table, arcade games, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
S$155
includes taxes & fees
8 Nov - 9 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 bathroom with a toilet, shower, and bathtub.
A modern apartment with a living room, kitchenette, and dining area.

7. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
S$141
includes taxes & fees
14 Oct - 15 Oct
The Central Downtown Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.
A bathroom with a bathtub, a sink, and a mirror.
A dining area with wooden tables and chairs, a television, and a door with a sign.

8. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
S$85
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 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.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

9. 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.
S$151
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 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.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

10. 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.
S$113
includes taxes & fees
18 Oct - 19 Oct
Howard Johnson by Wyndham Lenox
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

10/10 Excellent
"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."
Mark 1-night trip
Posted 15 hours ago
The Yankee Inn
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Clean room. Plenty of parking. Convenient breakfast"
Mateo 1-night trip
Posted 1 day ago
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"
Rohit 1-night trip
Posted 2 days ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great stay, very clean, super comfortable beds. Will def stay again when in the area."
Julia 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 2 days ago
The Red Lion Inn
Berkshire Inn

Berkshire Inn

10/10 Excellent
"We stayed one night after a concert at Tanglewood, and the hotel was perfectly fine for our purpose: clean and comfortable."
Mare 1-night trip
Posted 3 days ago
Berkshire Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 3 days ago
Quality Inn Great Barrington
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 4 days ago
The Central Downtown 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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