The Berkshires Hotel with Pool
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16 Aug - 17 AugTomorrow
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21 Aug - 23 AugIn two weeks
28 Aug - 30 AugOur top choices for The Berkshires hotels with a pool
1. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
HK$1,240
HK$1,385 total
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
- Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
HK$918
HK$1,179 total
includes taxes & fees
8 Sept - 9 Sept
3. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
HK$742
HK$1,004 total
includes taxes & fees
31 Aug - 1 Sept
4. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
HK$682
HK$847 total
includes taxes & fees
31 Aug - 1 Sept
5. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
HK$1,243
HK$1,778 total
includes taxes & fees
13 Sept - 14 Sept
6. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
- Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
HK$934
HK$1,043 total
includes taxes & fees
13 Sept - 14 Sept
7. The Little Lion
The Little LionGreat Barrington
- Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
HK$883
HK$986 total
includes taxes & fees
1 Sept - 2 Sept
8. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
- Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
HK$1,148
HK$1,282 total
includes taxes & fees
13 Sept - 14 Sept
View all properties
Hotels with pools and free breakfast in The Berkshires
HK$1,240
HK$1,385 total
includes taxes & fees
14 Sept - 15 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
HK$1,527
HK$1,706 total
includes taxes & fees
20 Aug - 21 Aug
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
HK$934
HK$1,043 total
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
HK$918
HK$1,179 total
includes taxes & fees
8 Sept - 9 Sept
HK$1,461
HK$1,632 total
includes taxes & fees
23 Aug - 24 Aug
HK$1,023
HK$1,143 total
includes taxes & fees
15 Sept - 16 Sept
HK$1,101
HK$1,230 total
includes taxes & fees
8 Sept - 9 Sept
HK$1,148
HK$1,282 total
includes taxes & fees
13 Sept - 14 Sept
HK$1,593
HK$1,779 total
includes taxes & fees
7 Sept - 8 Sept
HK$1,426
HK$1,769 total
includes taxes & fees
14 Sept - 15 Sept
4-star hotels with pools in The Berkshires
HK$3,052
HK$3,410 total
includes taxes & fees
3 Sept - 4 Sept
HK$2,958
HK$3,470 total
includes taxes & fees
13 Sept - 14 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodStockbridge
HK$2,591
HK$3,134 total
includes taxes & fees
31 Aug - 1 Sept
HK$2,502
HK$3,019 total
includes taxes & fees
1 Sept - 2 Sept
HK$1,718
HK$1,919 total
includes taxes & fees
10 Sept - 11 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
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Great location, spacious room, staff friendly and helpful."
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."
The Yankee Inn
8/10 Good
"It was very convenient for an overnight with pool and close to downtown. Affordable. I stayed in the annex so no noise from other guests!"
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."
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