The Best Family Hotels in Pittsfield, MA from AED 261 in 2026

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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.

1. Hotel On North

Pittsfield

AED 476 total

includes taxes & fees

29 Nov - 30 Nov

A hotel patio with outdoor seating and a fire pit.

2. Hilton Garden Inn Lenox Pittsfield

Pittsfield

AED 487 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

AED 406 total

includes taxes & fees

4 Dec - 5 Dec

A room with a pool table, arcade games, and seating areas.

4. Berkshire Mountain Lodge

Pittsfield

AED 397 total

includes taxes & fees

6 Dec - 7 Dec

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

5. 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.

AED 384 total

includes taxes & fees

1 Dec - 2 Dec

A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

6. 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.

AED 423 total

includes taxes & fees

4 Dec - 5 Dec

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

7. The Central Downtown Inn & Suites

Pittsfield

AED 406 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

Pittsfield

AED 292 total

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with a table and chairs, surrounded by a white railing.

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

AED 1,728 total

includes taxes & fees

7 Nov - 8 Nov

A bunk bed room with a wooden floor, a ladder, a wardrobe, and a window with curtains.

10. Hancock Village Inn Near Jiminy Peak

Hancock

AED 4,007 total

includes taxes & fees

17 Nov - 18 Nov

View all properties

Choose what matters most at family-friendly hotels in Pittsfield

Pool

Breakfast included

Top Pittsfield Hotel Reviews

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

t

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Gregory

The Central Downtown Inn & Suites

Pittsfield

10/10 Excellent

Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...

Anonymous traveler

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

10/10 Excellent

Gipsy

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A garden with a gazebo, a table, chairs, and potted plants.

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

A lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

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.

Find Family Hotels in Pittsfield, MA

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield family-friendly hotels

1. Hotel On North

2. Hilton Garden Inn Lenox Pittsfield

3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

4. Berkshire Mountain Lodge

5. Best Western Plus Berkshire Hills Inn & Suites

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

7. The Central Downtown Inn & Suites

8. FairBridge Inn Express

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

10. Hancock Village Inn Near Jiminy Peak

Choose what matters most at family-friendly hotels in Pittsfield

Top Pittsfield Hotel Reviews

Hotel On North

10/10 Excellent

Frequently Asked Questions

What's Pittsfield like for family-friendly vacations?

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

When’s the best time to book a family-friendly vacation in Pittsfield?

What's there to see and do with your family in Pittsfield?

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