Find Hotels with a Pool in Windsor, MA

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Check availability on Windsor Hotels with a Pool

Check prices for these dates

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Windsor Hotels with a Pool

Top Windsor Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Great location! Large comfortable room. "
Alisa 2-night trip
Posted 2 days ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

What are some accommodations with pools in Windsor?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Features free self parking, an indoor pool, and complimentary wireless internet access. The Williams Inn: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Provides 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Windsor?
Take a walk along the waterfront at Campers Beach and Iroquis Waterfront. Discover sights such as Mount Greylock State Reservation Visitor Center, Mount Greylock, and Barrington Stage Company during your stay.
When is the best time to book a hotel with a pool in Windsor?
Taking into account the local weather in Windsor can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.