Find Hotels with a Pool in The Berkshires, MA
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21 Aug - 23 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.
AED 606
AED 677 total
includes taxes & fees
7 Sep - 8 Sep
2. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
AED 576
AED 826 total
includes taxes & fees
9 Sep - 10 Sep
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.
AED 393
AED 511 total
includes taxes & fees
8 Sep - 9 Sep
4. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
AED 347
AED 470 total
includes taxes & fees
31 Aug - 1 Sep
5. 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.
AED 452
AED 505 total
includes taxes & fees
9 Sep - 10 Sep
AED 733
AED 994 total
includes taxes & fees
1 Sep - 2 Sep
7. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
AED 355
AED 437 total
includes taxes & fees
2 Sep - 3 Sep
8. 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.
AED 466
AED 521 total
includes taxes & fees
8 Sep - 9 Sep
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Hotels with pools and free breakfast in The Berkshires
AED 606
AED 677 total
includes taxes & fees
7 Sep - 8 Sep
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
AED 393
AED 511 total
includes taxes & fees
8 Sep - 9 Sep
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
AED 452
AED 505 total
includes taxes & fees
9 Sep - 10 Sep
AED 539
AED 602 total
includes taxes & fees
31 Aug - 1 Sep
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
AED 715
AED 799 total
includes taxes & fees
17 Aug - 18 Aug
AED 511
AED 571 total
includes taxes & fees
10 Sep - 11 Sep
AED 684
AED 764 total
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
AED 466
AED 521 total
includes taxes & fees
23 Aug - 24 Aug
AED 290
AED 324 total
includes taxes & fees
31 Aug - 1 Sep
AED 605
AED 676 total
includes taxes & fees
10 Sep - 11 Sep
4-star hotels with pools in The Berkshires
AED 1,429
AED 1,596 total
includes taxes & fees
3 Sep - 4 Sep
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
AED 1,213
AED 1,467 total
includes taxes & fees
24 Aug - 25 Aug
AED 1,171
AED 1,413 total
includes taxes & fees
1 Sep - 2 Sep
AED 1,450
AED 1,701 total
includes taxes & fees
8 Sep - 9 Sep
AED 804
AED 898 total
includes taxes & fees
10 Sep - 11 Sep
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 Red Lion Inn
10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
The Yankee Inn
8/10 Good
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Jiminy Peak Mountain Resort
10/10 Excellent
"Quiet and serene. Great weekend escape!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"
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