Find Hotels with a Pool in Windsor, MA from CA $105
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Our top choices for Windsor hotels with a pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (1,001 reviews)
- Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is CA $140
CA $156 total
includes taxes & fees
Mar 7 - Mar 8
9.8 out of 10, Exceptional, (18 reviews)
- Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is CA $191
CA $213 total
includes taxes & fees
Feb 22 - Feb 23
9.2 out of 10, Wonderful, (1,010 reviews)
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is CA $134
CA $150 total
includes taxes & fees
Feb 8 - Feb 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHGSouth Lee
9.0 out of 10, Wonderful, (832 reviews)
- Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is CA $154
CA $199 total
includes taxes & fees
Feb 9 - Feb 10
9.2 out of 10, Wonderful, (665 reviews)
- Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is CA $188
CA $210 total
includes taxes & fees
Feb 27 - Feb 28
7.6 out of 10, Good, (830 reviews)
- Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is CA $94
CA $105 total
includes taxes & fees
Feb 24 - Feb 25
8.8 out of 10, Excellent, (1,002 reviews)
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is CA $204
CA $290 total
includes taxes & fees
Mar 10 - Mar 11
9.2 out of 10, Wonderful, (1,000 reviews)
- Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is CA $163
CA $183 total
includes taxes & fees
Mar 1 - Mar 2
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.
Top Windsor Hotel Reviews
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
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