Find Hotels with a Pool in The Berkshires, MA
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25 Sep - 26 SepTomorrow
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2 Oct - 4 OctOur 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.
SAR 409
SAR 457 total
includes taxes & fees
25 Oct - 26 Oct
2. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
SAR 299
SAR 418 total
includes taxes & fees
21 Oct - 22 Oct
3. 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.
SAR 439
SAR 564 total
includes taxes & fees
27 Sep - 28 Sep
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.
SAR 357
SAR 440 total
includes taxes & fees
27 Sep - 28 Sep
5. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
SAR 443
SAR 495 total
includes taxes & fees
20 Oct - 21 Oct
6. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
SAR 605
SAR 862 total
includes taxes & fees
29 Sep - 30 Sep
7. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
- Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
SAR 561
SAR 626 total
includes taxes & fees
29 Sep - 30 Sep
8. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
- Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
SAR 507
SAR 567 total
includes taxes & fees
1 Oct - 2 Oct
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Hotels with pools and free breakfast in The Berkshires
SAR 409
SAR 457 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
SAR 439
SAR 564 total
includes taxes & fees
27 Sep - 28 Sep
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
SAR 443
SAR 495 total
includes taxes & fees
20 Oct - 21 Oct
SAR 561
SAR 626 total
includes taxes & fees
29 Sep - 30 Sep
SAR 549
SAR 614 total
includes taxes & fees
25 Oct - 26 Oct
SAR 467
SAR 522 total
includes taxes & fees
20 Oct - 21 Oct
SAR 635
SAR 709 total
includes taxes & fees
18 Oct - 19 Oct
SAR 507
SAR 567 total
includes taxes & fees
1 Oct - 2 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
SAR 635
SAR 709 total
includes taxes & fees
1 Oct - 2 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
SAR 402
SAR 449 total
includes taxes & fees
25 Oct - 26 Oct
4-star hotels with pools in The Berkshires
SAR 1,004
SAR 1,121 total
includes taxes & fees
27 Sep - 28 Sep
SAR 1,239
SAR 1,495 total
includes taxes & fees
28 Sep - 29 Sep
SAR 1,645
SAR 1,929 total
includes taxes & fees
27 Sep - 28 Sep
SAR 1,536
SAR 1,715 total
includes taxes & fees
25 Oct - 26 Oct
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
SAR 1,939
SAR 2,346 total
includes taxes & fees
12 Oct - 13 Oct
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
Hampton Inn & Suites Berkshires-Lenox
8/10 Good
"Toilet was faulty but they gave us another room. Not much variety on the breakfast"
Vacation Village in the Berkshires
10/10 Excellent
"great for families"
The Yankee Inn
10/10 Excellent
"No Pool or hot tub available"
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Jiminy Peak Mountain Resort
10/10 Excellent
"Even in the off season it was beautiful."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Good"