Family Hotels & Resorts in Pittsfield from NZ$135

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Check availability on Pittsfield Family Hotels

Our top choices for Pittsfield family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
"We have a dog traveling with us. It is really pet friendly. Love it!"
United States
Yan
The price is NZ$209
includes taxes & fees
21 May - 22 May
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Splash into family fun with indoor pool and spa pool—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
"Clean rooms, friendly staff, pool was very clean and so is the hot tub. Breakfast was okay. Overall our stay was excellent. Highly recommended."
United States
Camille
The price is NZ$241
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor dining

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!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is NZ$838
includes taxes & fees
27 May - 28 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
"kids had so much fun"
United States
Kristen
The price is NZ$217
includes taxes & fees
24 May - 25 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
6 bedrooms, in-room safe, iron/ironing board, free WiFi

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Lots of fun with family and friends."
United States
Danielle K.
The price is NZ$1,808
includes taxes & fees
20 May - 21 May
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
5.4 out of 10, (819 reviews)
"Parking good. Killed two cockroaches "
United States
John
The price is NZ$135
includes taxes & fees
2 June - 3 June
FairBridge Inn Express
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (906 reviews)
"The views from the property were beautiful. Parking was easy. The bathroom was lovely. "
United Kingdom
NICOLA
The price is NZ$160
includes taxes & fees
31 May - 1 June
Cozy Corner Motel
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
7.6 out of 10, Good, (579 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.
"Really nice little family business. Ty! "
United States
Raymond
The price is NZ$143
includes taxes & fees
27 May - 28 May
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.6 out of 10, Excellent, (1,010 reviews)
"After spending time with my family, the pool was very relaxing."
United States
Elizabeth
The price is NZ$222
includes taxes & fees
14 June - 15 June
Comfort Inn & Suites East Greenbush - Albany
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
"We wojld considrr returning in warmer weather with the kids/ grandkids as the environment is family friendly."
United States
Melody
The price is NZ$239
includes taxes & fees
27 May - 28 May
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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Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included

Top Pittsfield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Nothing fancy about it but it was all done right and was all very low key and at a great price"
David 3-night trip
Posted 6 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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?
Barrington Stage Company, Bousquet Ski Area and Colonial Theater 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 Berkshire Athenaeum and Crane Museum of Papermaking.
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.