Find Hotels with a Pool in The Berkshires, MA
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Check availability on The Berkshires Hotels with a Pool
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Aug 14 - Aug 15Tomorrow
Aug 15 - Aug 16This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23Our 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.
₩224,439
₩250,698 total
includes taxes & fees
Sep 14 - Sep 15
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.
₩165,801
₩212,905 total
includes taxes & fees
Sep 10 - Sep 11
3. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩134,373
₩181,829 total
includes taxes & fees
Aug 31 - Sep 1
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.
₩123,395
₩153,415 total
includes taxes & fees
Aug 31 - Sep 1
5. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩225,007
₩321,903 total
includes taxes & fees
Sep 13 - Sep 14
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.
₩169,040
₩188,817 total
includes taxes & fees
Sep 13 - Sep 14
7. The Little Lion
The Little LionGreat Barrington
- Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
₩159,424
₩178,077 total
includes taxes & fees
Sep 10 - Sep 11
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.
₩207,791
₩232,102 total
includes taxes & fees
Sep 13 - Sep 14
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Hotels with pools and free breakfast in The Berkshires
₩224,439
₩250,698 total
includes taxes & fees
Sep 14 - Sep 15
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
₩275,839
₩308,112 total
includes taxes & fees
Aug 19 - Aug 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
₩169,040
₩188,817 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
₩165,801
₩212,905 total
includes taxes & fees
Sep 10 - Sep 11
₩198,870
₩222,138 total
includes taxes & fees
Sep 3 - Sep 4
₩264,426
₩295,364 total
includes taxes & fees
Aug 19 - Aug 20
₩185,135
₩206,796 total
includes taxes & fees
Sep 13 - Sep 14
₩124,988
₩146,911 total
includes taxes & fees
Sep 9 - Sep 10
₩146,741
₩163,902 total
includes taxes & fees
Aug 16 - Aug 17
₩207,791
₩232,102 total
includes taxes & fees
Sep 13 - Sep 14
4-star hotels with pools in The Berkshires
₩552,575
₩617,222 total
includes taxes & fees
Sep 3 - Sep 4
₩535,500
₩628,074 total
includes taxes & fees
Sep 13 - Sep 14
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
₩467,884
₩566,003 total
includes taxes & fees
Aug 31 - Sep 1
₩452,870
₩546,481 total
includes taxes & fees
Sep 1 - Sep 2
₩310,947
₩347,326 total
includes taxes & fees
Sep 10 - Sep 11
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
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!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"The room was clean and the beds comfortable. The bathroom was small but nice. Lots of construction in the parking areas but luckily we got a parking space. Staff was friendly and helpful. We ate at the hotel, the food was good."
The Red Lion Inn
10/10 Excellent
"a very old building with tons of history and character. The room was very clean and comfortable and the staff was excellent...very friendly and accommodating."
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."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"