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
4 Sept - 5 Sept
Tomorrow
5 Sept - 6 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Pittsfield family-friendly hotels

1. 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.
RM363
RM406 total
includes taxes & fees
7 Sept - 8 Sept
Best Western Plus Berkshire Hills Inn & Suites

2. 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.
RM477
RM533 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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.
RM477
RM533 total
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

4. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
RM251
RM280 total
includes taxes & fees
10 Sept - 11 Sept
FairBridge Inn Express

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
RM515
RM576 total
includes taxes & fees
24 Sept - 25 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

6. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
RM788
RM881 total
includes taxes & fees
15 Sept - 16 Sept
Element by Marriott Lenox Berkshires

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
RM415
RM542 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
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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

The Yankee Inn

The Yankee Inn

8/10 Good
"The lounge was closed on Thursday. We went to a concert at Tanglewood and it would have been nice to have a nightcap. Might I suggest that you pole yiur guests and see if they are in town for a concert and if they would patronize the lounge if it was open."
Kenneth 1-night trip
Posted 10 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excellent customer service from front desk staff! Very nice decor everywhere. Fun little balcony! Quiet in the suite. All good!"
Leslieann H 1-night trip
Posted 10 hours ago
Vacation Village in the Berkshires
FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"The exterior is scary. The lobby is a fright. Rooms however were clean and updated. I appreciate that. But the lot is a disgrace."
Janet 1-night trip
Posted 16 hours ago
FairBridge Inn Express
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel was clean and stag was helpful and friendly."
Basil 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
James 2-night trip
Posted 2 days ago
The Red Lion Inn
Berkshire Inn

Berkshire Inn

8/10 Good
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
Ellen 1-night trip
Posted 2 days ago
Berkshire Inn
Hotel On North

Hotel On North

8/10 Good
"Nice room! Comfortable bed. Super friendly staff."
Jana 1-night trip
Posted 4 days ago
Hotel On North
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Clean comfortable; difficult to see sign locating property"
Doreen 1-night trip
Posted 13 days ago
Hilton Garden Inn Lenox Pittsfield

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 Holiday Inn & Suites Pittsfield-Berkshires by IHG and Best Western Plus Berkshire Hills Inn & Suites.
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, Barrington Stage Company and Bousquet Ski Area 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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