Family Hotels & Resorts in The Berkshires from AU$146
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28 Aug - 30 AugOur top choices for The Berkshires family-friendly hotels
1. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
AU$212
includes taxes & fees
8 Sept - 9 Sept
2. 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.
AU$201
includes taxes & fees
14 Sept - 15 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 spa pool—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
AU$188
includes taxes & fees
14 Sept - 15 Sept
4. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
- Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cosy rooms—all nestled near Ski Butternut.
AU$307
includes taxes & fees
23 Aug - 24 Aug
5. 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.
AU$180
includes taxes & fees
30 Aug - 31 Aug
AU$146
includes taxes & fees
9 Sept - 10 Sept
AU$197
includes taxes & fees
9 Sept - 10 Sept
8. 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.
AU$200
includes taxes & fees
23 Aug - 24 Aug
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Family-friendly hotels with free breakfast in The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
AU$212
includes taxes & fees
8 Sept - 9 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
AU$201
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
AU$188
includes taxes & fees
14 Sept - 15 Sept
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
AU$180
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
AU$200
includes taxes & fees
23 Aug - 24 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
AU$307
includes taxes & fees
23 Aug - 24 Aug
AU$146
includes taxes & fees
9 Sept - 10 Sept
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
AU$125
includes taxes & fees
1 Sept - 2 Sept
AU$320
includes taxes & fees
7 Sept - 8 Sept
AU$106
includes taxes & fees
7 Sept - 8 Sept
Family-friendly hotels with pools in The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
AU$212
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
AU$188
includes taxes & fees
14 Sept - 15 Sept
AU$218
includes taxes & fees
2 Sept - 3 Sept
AU$146
includes taxes & fees
9 Sept - 10 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
AU$307
includes taxes & fees
23 Aug - 24 Aug
AU$197
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
AU$200
includes taxes & fees
23 Aug - 24 Aug
AU$320
includes taxes & fees
7 Sept - 8 Sept
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
2 BR Jiminy Peak w Mountain View Sleeps 7 GorgeousHancock
AU$486
includes taxes & fees
18 Aug - 19 Aug
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous InnHancock
AU$345
includes taxes & fees
19 Aug - 20 Aug
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.
View all propertiesTop The Berkshires Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Hotel On North
10/10 Excellent
"Big rooms. Very good staff. Access to big gym. Easy parking."
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."
The Cornell Inn, Lenox & The Berkshires
8/10 Good
"Bed not very comfortable.."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
Jiminy Peak Mountain Resort
10/10 Excellent
"Only problem was the stairs. I hadn't realized that there was such a long climb to our condo or I would have asked for something a little friendlier to a 75 year old."
FairBridge Inn Express
10/10 Excellent
"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."
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