Find Windsor Hotels with Swimming Pool

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Hotels with Swimming Pools in Windsor

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

What are some accommodation options with pools in Windsor?
The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. Life House Berkshires: Provides a seasonal outdoor pool, an indoor pool and buffet. The Yankee, Trademark Collection by Wyndham: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Black Swan Lee - Lenox, Ascend Hotel Collection: Features 2 indoor swimming pools, 2 outdoor swimming pools and 2 restaurants. Hotel Downstreet: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access.
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 Savoy Mountain State Forest, Mount Greylock State Reservation Visitor Center and Mohawk Trail State Forest during your stay.
When is the best time to book a hotel with a pool in Windsor?
Taking the local weather in Windsor into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.