Family friendly Hotels, Pittsfield Massachusetts

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Check availability on Pittsfield Family friendly Hotels

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Our top choices for Pittsfield family-friendly hotels

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.

A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

1. 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.

P6,685

P7,467 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

2. 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.

P6,609

P7,382 total

includes taxes & fees

Oct 18 - Oct 19

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A modern cafe with a counter, seating area, and large windows.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

3. 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 Center.

P7,122

P7,956 total

includes taxes & fees

Oct 20 - Oct 21

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 hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

A dining area with wooden tables and chairs, a television, and a door with a sign.

4. FairBridge Inn Express

Pittsfield

P3,880

P4,334 total

includes taxes & fees

Sep 28 - Sep 29

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 dining area with large windows, wooden furniture, and a view of a lake.

A lakeside dock with kayaks and a covered boat ramp.

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

Lee

Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.

P8,606

P9,613 total

includes taxes & fees

Sep 29 - Sep 30

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

An outdoor seating area with Adirondack chairs and a fire feature.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

6. Element by Marriott Lenox Berkshires

Lenox

P10,558

P11,794 total

includes taxes & fees

Oct 18 - Oct 19

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 building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

P7,310

P9,386 total

includes taxes & fees

Sep 29 - Sep 30

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 wooden deck with a table and chairs, overlooking a road with a sign for 'Holliday Lodge'.

A hotel room with a bed, a desk, and two wall-mounted lamps.

A small, compact bathroom with a toilet, sink, and a mirror above it.

8. Econo Lodge Lee - Great Barrington

Lee

Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.

P4,355

P4,864 total

includes taxes & fees

Oct 25 - Oct 26

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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

10/10 Excellent

"It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any of the amenities that they charge extra for, but because I was traveling, it was nice to just have a quiet night in."

The Red Lion Inn

10/10 Excellent

"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."

Quality Inn Great Barrington

10/10 Excellent

"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"Overall, this place is not bad and it's convenient to the Albany area. There is also a Stewarts and a Dunkin's within a short walk. While breakfast was advertised as "included," the morning crew that prepares it was late forcing me to eat something less than what was advertised. Bummer."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."

Berkshire Inn

10/10 Excellent

"Good"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Nice place, would stay again"

Frequently asked questions

What's Pittsfield like for family-friendly vacations?

If you've been thinking about a trip with your kids, the historic destination of Pittsfield is a good choice. The biking 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 center.

What's the best hotel when traveling with kids to 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 choices 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 vacation in Pittsfield?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches 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 you and your family will enjoy exploring while you are staying in Pittsfield. Make sure you have lots of time for activities like Guido's Marketplace and Berkshire Athenaeum.

What's the best way for us to get around Pittsfield?

To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options so consider renting a car to explore more.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Family friendly Hotels

Our top choices for Pittsfield family-friendly hotels

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

2. Best Western Plus Berkshire Hills Inn & Suites