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Check availability on Pittsfield Family-Friendly Hotels

Top Pittsfield Family-Friendly Hotels

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cots/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 1.724.434 ₫
1.926.194 ₫ total
includes taxes & fees
24 Nov - 25 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
  • Cots/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (60)
Vacation-ready accommodation feature premium TV channels and complimentary cots for little travellers. Mornings begin with a free breakfast buffet, fuelling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is 2.777.606 ₫
3.102.586 ₫ 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
  • Cots/infant beds provided
  • Indoor pool
8.0 out of 10, Very good, (961)
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 cots and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is 2.324.070 ₫
2.595.987 ₫ total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 1.976.250 ₫
2.207.603 ₫ total
includes taxes & fees
27 Nov - 28 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 3.557.655 ₫
3.973.900 ₫ 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 1.968.345 ₫
2.323.543 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Cozy Corner Motel
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
9.6 out of 10, Exceptional, (14)
The price is 6.851.780 ₫
8.536.527 ₫ 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
  • Cots/infant beds provided
9.0 out of 10, Wonderful, (1002)
Playtime paradise awaits with free cots, 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 2.889.278 ₫
3.227.324 ₫ total
includes taxes & fees
19 Dec - 20 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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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.
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 Berkshire Athenaeum 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 Barrington Stage Company and Guido's Marketplace.
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.