Find Hotels with a Pool in Windsor, MA
Check availability on Windsor Hotels with a Pool
Our top choices for Windsor hotels with a pool
8.8 out of 10, Excellent, (1,003 reviews)
- Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
$161 nightly
The price is $179
Aug 16 - Aug 17
Total with taxes and fees
9.2 out of 10, Wonderful, (1,009 reviews)
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$195 nightly
The price is $218
Jul 22 - Jul 23
Total with taxes and fees
8.8 out of 10, Excellent, (2,463 reviews)
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
$153 nightly
The price is $171
Jul 22 - Jul 23
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (1,004 reviews)
- Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
$130 nightly
The price is $145
Jul 26 - Jul 27
Total with taxes and fees
9.2 out of 10, Wonderful, (108 reviews)
- Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
$142 nightly
The price is $156
Jul 22 - Jul 23
Total with taxes and fees
7.8 out of 10, Good, (887 reviews)
- Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
$90 nightly
The price is $101
Jul 22 - Jul 23
Total with taxes and fees
7.6 out of 10, Good, (885 reviews)
- Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$99 nightly
The price is $111
Jul 22 - Jul 23
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
9.4 out of 10, Exceptional, (138 reviews)
- Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
$145 nightly
The price is $162
Jul 26 - Jul 27
Total with taxes and fees
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
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
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