Photo by Hyelsinta

Hotels with a Pool in Winchester

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Apr 25 - Apr 26
Tomorrow
Apr 26 - Apr 27
This weekend
Apr 25 - Apr 27
Next weekend
May 2 - May 4

Hotels with a Pool in Winchester

Baymont by Wyndham Winchester
Desk, laptop workspace, iron/ironing board, free WiFi

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (662)
The price is $88
includes taxes & fees
$80 per night
May 11 - May 12
Baymont by Wyndham 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.

Top landmarks in Winchester

Bluegrass Heritage Museum

The centre of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Clark Regional Medical Center, Lykins Park, and Southwind Golf Course.

See properties in Bluegrass Heritage Museum
Bluegrass Heritage Museum

Frequently asked questions

What are the best hotels with a pool in Winchester?
According to guest reviews, Hampton Inn Winchester is one of the best Winchester hotels with a pool. blackout curtains and front desk services are included in your stay too. Holiday Inn Express Lexington East - Winchester, an IHG Hotel is another visitor favorite where you can go for a swim. To explore other popular options with this perk, select the “Pool” filter and then sort by “Guest rating + our picks.”
What are the cheapest hotels with a pool in Winchester?
You’ll find some great-value hotels in Winchester with a pool for your next adventure. Featuring express check-out services and nearby historical attractions, Hampton Inn Winchester is one of the cheapest. Holiday Inn Express Lexington East - Winchester, an IHG Hotel is another option that delivers poolside fun on a budget.
What is the best time to stay in a hotel with a pool in Winchester?
July is the warmest month, with temperatures ranging from 66ºF (19ºC) to 86ºF (30ºC). January sees the coolest weather. It’s usually between 27ºF (-3ºC) and 37ºF (3ºC) at this time. January is a great month to enjoy a more relaxed pace and potentially lock in cheaper Winchester hotels with a pool.
What hotels with a pool are closest to Bluegrass Heritage Museum?
Just a short drive from Bluegrass Heritage Museum, Hampton Inn Winchester is one of the closest hotels with a pool. It comes with express check-out services and soundproofed rooms too. Another nearby option is Best Western Winchester Hotel. Book a hotel in Winchester with a pool close to this attraction for the perfect way to recharge after a day of sightseeing.
What hotels with a pool are closest to Blue Grass Airport (LEX)?
Around 2 miles northwest of Blue Grass Airport (LEX), Chateau Annette is a top pick. Recharge with a swim after your flight and take advantage of a free cooked-to-order breakfast and complimentary breakfast here. TownePlace Suites by Marriott Lexington Keeneland/Airport is another nearby property. Choose a Winchester hotel with a pool close to the airport and make your stay all about convenience and comfort.
Are there any hotels with a pool in Winchester with parking?
You’ll find 1,111 Winchester hotels with a pool and parking. Pull in and go for a dip at Hampton Inn Winchester. Express check-out services and soundproofed rooms are included in your stay too. Or, head to Holiday Inn Express Lexington East - Winchester, an IHG Hotel, where you can easily access both parking and a pool.