Find Kid Friendly Hotels in Pittsfield from S$101

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Check availability on Pittsfield Family friendly Hotels

Tonight
2 Jul - 3 Jul
Tomorrow
3 Jul - 4 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Family friendly Hotels in Pittsfield

Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (742)
"Great boutique hotel"
The price is S$270
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1009)
"Great place to stay "
The price is S$168
includes taxes & fees
13 Jul - 14 Jul
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (808)
"Staff was welcoming and informative "
The price is S$175
includes taxes & fees
24 Jul - 25 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (777)
"The motel was nicely done and clean. The beds were comfortable "
The price is S$131
includes taxes & fees
8 Jul - 9 Jul
Berkshire Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (733)
"Shampoo and toilet paper should have been In the room."
The price is S$101
includes taxes & fees
15 Jul - 16 Jul
FairBridge Inn Express
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$319
includes taxes & fees
14 Jul - 15 Jul
Hilton Garden Inn Lenox Pittsfield
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (290)
"Very nice place to stay. Recently upgraded. Great location and convenient parking."
The price is S$169
includes taxes & fees
28 Jul - 29 Jul
The Central Downtown Inn & Suites
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.

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?
Best Western Plus Berkshire Hills Inn & Suites is a hotel with free parking and free breakfast, 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 Holiday Inn Express & Suites Pittsfield - Berkshires.
How many hotels that welcome families will I find in Pittsfield?
Expedia has 8 family-friendly hotels and other accommodation options in Pittsfield.
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 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.