The Berkshires Hotel Guide - Family Friendly Hotels in The Berkshires, Massachusetts
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25 Aug - 26 AugTomorrow
26 Aug - 27 AugThis weekend
28 Aug - 30 AugNext weekend
4 Sept - 6 SeptOur top choices for The Berkshires family-friendly hotels
1. 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.
€122
includes taxes & fees
14 Sept - 15 Sept
2. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
€129
includes taxes & fees
9 Sept - 10 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.
€114
includes taxes & fees
24 Sept - 25 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.
€186
includes taxes & fees
1 Sept - 2 Sept
€89
includes taxes & fees
9 Sept - 10 Sept
6. 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.
€109
includes taxes & fees
7 Sept - 8 Sept
7. 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.
€114
includes taxes & fees
22 Sept - 23 Sept
€187
includes taxes & fees
31 Aug - 1 Sept
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Family-friendly hotels with free breakfast in The Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
€122
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
€129
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
€114
includes taxes & fees
24 Sept - 25 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
€186
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
€114
includes taxes & fees
22 Sept - 23 Sept
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
€109
includes taxes & fees
7 Sept - 8 Sept
€187
includes taxes & fees
31 Aug - 1 Sept
€89
includes taxes & fees
9 Sept - 10 Sept
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
€76
includes taxes & fees
1 Sept - 2 Sept
€120
includes taxes & fees
9 Sept - 10 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
€129
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
€114
includes taxes & fees
24 Sept - 25 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
€186
includes taxes & fees
1 Sept - 2 Sept
€187
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
€114
includes taxes & fees
22 Sept - 23 Sept
€89
includes taxes & fees
9 Sept - 10 Sept
€137
includes taxes & fees
30 Aug - 31 Aug
€120
includes taxes & fees
9 Sept - 10 Sept
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
€211
includes taxes & fees
26 Aug - 27 Aug
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
2 BR Jiminy Peak w Mountain View Sleeps 7 GorgeousHancock
€306
includes taxes & fees
23 Sept - 24 Sept
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
Quality Inn Great Barrington
10/10 Excellent
"If you're looking for a nice basic hotel with breakfast and free parking, I highly recommend this Quality Inn in Great Barrington, MA. Our room was clean, comfortable, and well priced. Breakfast included a nice variety of hot and cold food items. The scrambled eggs and sausage links were very tasty, and so were the make-your-own waffles. The staff were very nice. I look forward to returning. Note: A freight rail line runs through Great Barrington once a day."
Hotel On North
10/10 Excellent
"Such a comfortable hotel and the art and decor made for a unique stay!"
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"BIen situé avec pleins de restaurants accessibe à pied autour. Grand parking sécuritaire en face il y a la caserne de pompiers. Idéalement ce serait bien d'installer des bornes électriques de recharge pour les véhicules électriques. Déjeuner modeste. Pas de protéines. Pâtisseries et fruits bons. Très propre. Personnel courtois"
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
FairBridge Inn Express
10/10 Excellent
"It was very nice and everyone was extremely helpful"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
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