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
    Sign in
    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.
Unlock Black Friday deals

Frequently asked questions

What are some accommodation options with pools in Winchester?
Super 8 by Wyndham Giddings: Features daily, a seasonal outdoor pool and free self parking. The Enchanting Hobbit’s Nest Treehouse- A Magical Escape in the Lost Pines Shire: Provides daily, a seasonal outdoor pool and free self parking. Days Inn by Wyndham Bastrop: Features full, an outdoor pool and complimentary high-speed (wired) Internet access. Best Western La Grange Inn & Suites: Offers a pool and air conditioning. Enchanting Dog-Friendly Treehouse- The Elf’s Aerie in the Lost Pines Shire: Offers daily, an outdoor pool and free self parking.
What is there to see and do in Winchester?
The picturesque settings of Buescher State Park and Lester Park showcase the area’s natural beauty. Discover sights such as Bluff Creek Ranch, World’s Largest Gingerbread Man and Fayette County Courthouse during your stay.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider accommodation with an outdoor swimming pool if you’re planning to visit Winchester in the hottest months of August, July or June, when the average temperature is 28°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temperature is 13°C.