Hotels with Swimming Pool, Winchester Lexington

Q: What are some accommodations with pools in Winchester?

Baymont by Wyndham Winchester : Features daily, a pool, and free self parking. Best Western Winchester Hotel : Offers full, a seasonal outdoor pool, and free self parking.

An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Winchester Hotels with Swimming Pool

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Winchester hotels with a pool

Best Western Winchester Hotel

Winchester

Splash into summer at this serene pool oasis where tranquil waters meet exceptional service.

P6,420 total

includes taxes & fees

Jun 29 - Jun 30

Baymont by Wyndham Winchester

Winchester

Refreshing year-round aquatic escape awaits at this Winchester hotel's indoor pool, complemented by a modern fitness center.

P5,171 total

includes taxes & fees

Jul 26 - Jul 27

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Dive into aquatic bliss in this rural retreat with an indoor pool open from dawn to dusk.

P8,246 total

includes taxes & fees

Jul 28 - Jul 29

Hampton Inn Winchester

Winchester

Seasonal outdoor pool creates refreshing summer sanctuary at this hotel, offering a peaceful retreat in the heart of Winchester.

P9,034 total

includes taxes & fees

Jul 29 - Jul 30

Natural Bridge State Resort Park

Slade

Dive into summer splendor at this seasonal outdoor pool with mountain views and natural surroundings.

P8,574 total

includes taxes & fees

Jul 12 - Jul 13

Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

Holiday Inn Express Lexington Horse Park Area by IHG

Lexington

Float in pristine waters at this Art Deco hotel with an indoor pool and poolside sun loungers for ultimate relaxation.

P7,330 total

includes taxes & fees

Jul 21 - Jul 22

Comfort Inn & Suites Mount Sterling

Mount Sterling

Soothing indoor pool oasis for relaxation awaits at this hotel with a steamy hot tub retreat.

P6,779 total

includes taxes & fees

Jul 29 - Jul 30

Country Inn & Suites by Radisson, Georgetown, KY

Georgetown

Make a splash at this hotel's indoor pool paradise with hot tub for total relaxation.

P4,840 total

includes taxes & fees

Jul 26 - Jul 27

View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Top Winchester Hotel Reviews

The Campbell House Lexington, Curio Collection by Hilton

8/10 Good

"Beautiful property and very clean, just needs a few maintenance updates, but the property is very old and historic."

Frequently asked questions

What are some accommodations with pools in Winchester?

Baymont by Wyndham Winchester: Features daily, a pool, and free self parking. Best Western Winchester Hotel: Offers full, a seasonal outdoor pool, and free self parking.

What is there to see and do in Winchester?

Spend some time experiencing the great outdoors at Community Park and The Holler. During your stay, check out sights such as Bluegrass Heritage Museum, Wiseman Park, and Winchester Traveling Trail. You'll also discover lots of options for restaurants in Winchester.

When is the best time to book a hotel with a pool in Winchester?

You may want to consider a place to stay that offers an outdoor pool if you plan to visit Winchester in the hottest months of July, August, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 38°F.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Winchester Hotels with Swimming Pool