Photo by Donny Campos

Hotels with Pool & Resorts in Winchester

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Best Winchester Hotels with Pool

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.

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Offers a sauna, an indoor pool and free self parking. The Covered Bridge Inn: Features a full-service spa, 2 indoor swimming pools and a sauna. Colonial Motel And Spa: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hampton Inn Brattleboro: Offers buffet, an indoor pool and free self parking. The Putney Inn: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions such as Pisgah State Park and Rhododendron State Park. Discover sights such as Ashuelot River and Birch Point during your stay. Take in the natural beauty of Winchester with the lakeside setting.
When is the best time to book a hotel with a pool in Winchester?
Taking the local weather in Winchester 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 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.