Find Family Hotels in Pittsfield, MA

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Check availability on Pittsfield Family Hotels

Top Pittsfield Family Hotels

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cribs/infant beds
8.6 out of 10, Excellent, (1000)
Family memories await at this thoughtful property, featuring spacious suites with premium TV channels and blackout drapes for restful evenings. Complimentary breakfast fuels adventures before heading to nearby Bousquet Ski Area, just a quick 5-minute drive away.
The price is AED 240
AED 268 total
includes taxes & fees
23 Nov - 24 Nov
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (60)
Vacation-ready accommodations feature premium TV channels and complimentary cribs for little travelers. Mornings begin with a free breakfast buffet, fueling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is AED 387
AED 432 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
8.0 out of 10, Very Good, (962)
Spacious suites accommodate families with comfort, while children splash in the heated indoor pool year-round. Located steps from Berkshire Museum, this hotel offers complimentary cribs and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is AED 324
AED 362 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

2.0 star property
Pittsfield
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Outdoor Space
7.8 out of 10, Good, (6)
The price is AED 988
AED 1,814 total
includes taxes & fees
20 Nov - 21 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
  • Arcade/game room
10.0 out of 10, Exceptional, (15)
The price is AED 2,163
AED 4,036 total
includes taxes & fees
19 Nov - 20 Nov
Hancock Village Inn Near Jiminy Peak
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
  • Laundry
  • Housekeeping
5.4 out of 10, (810)
The price is AED 275
AED 308 total
includes taxes & fees
19 Nov - 20 Nov
FairBridge Inn Express
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.6 out of 10, Exceptional, (10)
The price is AED 496
AED 554 total
includes taxes & fees
30 Nov - 1 Dec
Element Lenox Berkshires
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Business services
9.2 out of 10, Wonderful, (882)
The price is AED 274
AED 324 total
includes taxes & fees
19 Nov - 20 Nov
Cozy Corner Motel
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
9.6 out of 10, Exceptional, (14)
The price is AED 955
AED 1,190 total
includes taxes & fees
24 Nov - 25 Nov
Prospect Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1000)
Playtime paradise awaits with free cribs, kayaking on the sparkling lake, and motor boating adventures. Children delight in fishing excursions, premium TV entertainment, and beachside fun while parents appreciate the lakefront setting and complimentary breakfast each morning.
The price is AED 403
AED 450 total
includes taxes & fees
8 Dec - 9 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities "
Teresa 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires

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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 - 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 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 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 Berkshire Athenaeum 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 Barrington Stage Company and Guido's Marketplace.
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.