Hotels with Pool & Resorts in The Berkshires from AU$168
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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.
AU$261
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.
AU$197
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 spa pool experiences.
AU$181
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.
AU$168
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.
AU$319
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.
AU$195
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 spa pool to soothe tired muscles.
AU$201
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.
AU$178
includes taxes & fees
1 Sept - 2 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
AU$197
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
AU$195
includes taxes & fees
9 Sept - 10 Sept
AU$232
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
AU$308
includes taxes & fees
17 Aug - 18 Aug
AU$220
includes taxes & fees
9 Sept - 10 Sept
AU$295
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
AU$201
includes taxes & fees
27 Aug - 28 Aug
AU$125
includes taxes & fees
31 Aug - 1 Sept
AU$261
includes taxes & fees
10 Sept - 11 Sept
4-star hotels with pools in The Berkshires
AU$615
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
AU$565
includes taxes & fees
26 Aug - 27 Aug
AU$545
includes taxes & fees
1 Sept - 2 Sept
AU$667
includes taxes & fees
7 Sept - 8 Sept
AU$348
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
Vacation Village in the Berkshires
8/10 Good
"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."
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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