Hotels with Swimming Pools in The Berkshires
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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.
S$236
includes taxes & fees
7 Sept - 8 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.
S$178
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.
S$164
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.
S$152
includes taxes & fees
2 Sept - 3 Sept
5. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
S$288
includes taxes & fees
9 Sept - 10 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.
S$176
includes taxes & fees
9 Sept - 10 Sept
7. 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.
S$181
includes taxes & fees
8 Sept - 9 Sept
8. The Little Lion
The Little LionGreat Barrington
- Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
S$161
includes taxes & fees
7 Sept - 8 Sept
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Hotels with pools and free breakfast in The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
S$178
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
S$176
includes taxes & fees
9 Sept - 10 Sept
S$210
includes taxes & fees
31 Aug - 1 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
S$278
includes taxes & fees
20 Aug - 21 Aug
S$199
includes taxes & fees
9 Sept - 10 Sept
S$266
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
S$181
includes taxes & fees
23 Aug - 24 Aug
S$113
includes taxes & fees
31 Aug - 1 Sept
S$236
includes taxes & fees
10 Sept - 11 Sept
4-star hotels with pools in The Berkshires
S$556
includes taxes & fees
3 Sept - 4 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
S$511
includes taxes & fees
7 Sept - 8 Sept
S$493
includes taxes & fees
1 Sept - 2 Sept
S$592
includes taxes & fees
7 Sept - 8 Sept
S$313
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
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."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Love this hotel for going to Mass MoCA"
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"
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