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Hotels with a Pool in Winchester

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Hotels with a Pool in Winchester

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.
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Top landmarks in Winchester

Frequently asked questions

What are the best hotels with a pool in Winchester?
With there are nearby historical attractions, front desk services and the perfect setting for unwinding by the water, Hampton Inn Winchester is a hit with travelers. Holiday Inn Express Lexington East - Winchester, an IHG Hotel is another popular Winchester hotel with a pool.
What are the cheapest hotels with a pool in Winchester?
Hampton Inn Winchester is one of the cheapest stays with a pool in Winchester. It also offers front desk services and blackout curtains. Holiday Inn Express Lexington East - Winchester, an IHG Hotel is another option that delivers poolside fun on a budget. Check out the range of great-value hotels in Winchester with a pool and live it up for less.
What is the best time to stay in a hotel with a pool in Winchester?
If you’d like to explore when crowds are smaller, go in January. You could find some amazing deals on Winchester hotels with a pool around then. The warmest time of year is in July, with temperatures ranging from 66ºF (19ºC) to 86ºF (30ºC). It’s coolest in January, when averages are between 27ºF (-3ºC) and 37ºF (3ºC).
What hotels with a pool are closest to Bluegrass Heritage Museum?
Just a quick drive from Bluegrass Heritage Museum, Hampton Inn Winchester is one of the closest hotels with a pool. It also comes with express check-out services and soundproofed rooms. Another option nearby is Best Western Winchester Hotel. Stay in a hotel in Winchester with a pool close to this attraction for the perfect way to unwind after a busy day.
What hotels with a pool are closest to Blue Grass Airport (LEX)?
Go from your plane seat to paddling around in the pool at Chateau Annette. It’s located around 2 miles northwest of Blue Grass Airport (LEX) and also offers a free cooked-to-order breakfast and complimentary breakfast. TownePlace Suites by Marriott Lexington Keeneland/Airport is another option close by. Whether you’re staying a while or on a stopover, find a Winchester hotel with a pool close to the airport and combine relaxation with convenience.
Are there any hotels with a pool in Winchester with parking?
You’ll find Winchester hotels with a pool and parking. Pull up and go for a dip at Hampton Inn Winchester. This escape also has express check-out services and soundproofed rooms. Or, head to Holiday Inn Express Lexington East - Winchester, an IHG Hotel, where you can easily access both parking and a pool.