Search Family-Friendly Hotels in Pittsfield
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Pittsfield Family-Friendly Hotels
Tonight
20 Aug - 21 AugTomorrow
21 Aug - 22 AugThis weekend
21 Aug - 23 AugNext weekend
28 Aug - 30 AugOur top choices for Pittsfield family-friendly hotels
1. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
฿3,912
฿4,369 total
includes taxes & fees
17 Sept - 18 Sept
2. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
- Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
฿3,747
฿4,185 total
includes taxes & fees
1 Sept - 2 Sept
3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
฿4,175
฿4,663 total
includes taxes & fees
14 Sept - 15 Sept
฿2,041
฿2,280 total
includes taxes & fees
24 Aug - 25 Aug
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
- Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
฿4,191
฿4,682 total
includes taxes & fees
14 Sept - 15 Sept
฿6,114
฿6,830 total
includes taxes & fees
31 Aug - 1 Sept
7. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
฿3,846
฿4,939 total
includes taxes & fees
3 Sept - 4 Sept
8. Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
- Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
฿4,704
฿5,254 total
includes taxes & fees
30 Aug - 31 Aug
Top Pittsfield Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
The Yankee Inn
10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Berkshire Inn
8/10 Good
"Hotels in the Lenox area are dramatically over-priced this time of year (Tanglewood, I trust). Berkshire Inn was the one with a bit more reasonable price and a good rating. We were pleased to find that the rooms were just as pictured... clean, neat and must have had a recent (very attractive) renovation. Very comfortable overnight stay in a motel with almost no amenities, friendly gentleman in the office and, while still over-priced, not quite at the extreme level of all other area options."
The Red Lion Inn
10/10 Excellent
"Perfect."
Howard Johnson by Wyndham Lenox
8/10 Good
"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."
The Central Downtown Inn & Suites
10/10 Excellent
"Not easy to follow find. Bit of a AI STAFF. Once we fould it it was very nice."
Hotel On North
10/10 Excellent
"A great location for a concert at Tanglewood and a chance to explore a new city. Parking is easy and convenient. The staff is very welcoming and helpful. The facilities are clean, modern, quiet, and vintage at the same time. A beautiful bar and restaurant on site and many restaurants and coffee shops in walking distance. I would definitely stay here again!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."