Pittsfield Hotel Guide - Family Friendly Hotels in Pittsfield, Massachusetts

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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, (1001)
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 €91
includes taxes & fees
23 Nov - 24 Nov
Best Western Plus Berkshire Hills Inn & Suites
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, (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 cots and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is €86
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 €96
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & 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 €438
includes taxes & fees
23 Nov - 24 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/games room
10.0 out of 10, Exceptional, (15)
The price is €989
includes taxes & fees
9 Dec - 10 Dec
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 €73
includes taxes & fees
23 Nov - 24 Nov
FairBridge Inn Express
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
The price is €127
includes taxes & fees
15 Dec - 16 Dec
Element Lenox Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Cots/infant beds provided
7.6 out of 10, Good, (559)
Family holidays shine at this peaceful Berkshire retreat offering complimentary cots and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodation and helpful staff ensure carefree comfort for travellers of all ages.
The price is €73
includes taxes & fees
22 Nov - 23 Nov
Travelodge by Wyndham Great Barrington Berkshires
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (1005)
Splash into family fun at this hotel with dual pools, kid-friendly supervised swimming, and microwaves for quick snacks. Just a 3-minute drive from Bousquet Ski Area, the property combines mountain scenery with cosy rooms featuring cable TV and essential comforts.
The price is €80
includes taxes & fees
5 Dec - 6 Dec
The Yankee, Trademark Collection by Wyndham
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 €76
includes taxes & fees
2 Dec - 3 Dec
Cozy Corner Motel
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank 1-night trip
Posted 5 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Frequently asked questions

What's Pittsfield like for family-friendly holidays?
The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your children. The cycling trails, entertainment and lake views are just some of the things that make this a good destination for family holidays. 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 & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your family trip include Holiday Inn Express & 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, 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.