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.

Hotels with Swimming Pool in Winchester, Lexington

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Check availability on Winchester Hotels with Swimming Pool

Our top choices for Winchester hotels with a pool

A swimming pool with a no diving sign, lounge chairs, and a building with a no diving sign.

1. Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (487 reviews)
"Close to Red River Gorge hiking."
United States
kelly
The price is P6,956
P7,668 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Winchester
A rectangular swimming pool with a white edge, surrounded by a concrete deck and a low white wall.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
"They have a really good Breakfast..."
United States
David
The price is P5,381
P5,932 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Winchester Hotel
A swimming pool with wooden walls and large windows offering views of greenery.

3. Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.4 out of 10, Good, (867 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is P5,023
P5,538 total
includes taxes & fees
Nov 19 - Nov 20
Baymont by Wyndham Winchester
An indoor swimming pool with a lifeguard chair, a pool ladder, and a sign indicating no diving allowed.

4. Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (616 reviews)
"This is one of the nicest and cleanest Holiday Inns I’ve ever been to. Very friendly staff too."
United States
Stephen
The price is P6,902
P7,609 total
includes taxes & fees
Nov 14 - Nov 15
Holiday Inn Express Lexington East - Winchester by IHG
A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

5. Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (201 reviews)
"Room was clean"
United States
Kristie
The price is P3,714
P4,094 total
includes taxes & fees
Nov 20 - Nov 21
Value Stay
An indoor swimming pool with tiled flooring, orange walls, and potted plants.

6. Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (397 reviews)
"Pool was closed other than that overall good hotel"
United States
james
The price is P4,922
P5,427 total
includes taxes & fees
Dec 2 - Dec 3
Comfort Inn 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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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

Top Winchester Hotel Reviews

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Will stay again! Convenient and clean."
Margaret 2-night trip
Posted 1 day ago
Hilton Lexington/Downtown

Frequently asked questions

What are some accommodations with pools in Winchester?
Best Western Winchester Hotel: Features full, a seasonal outdoor pool, and free self parking. Baymont by Wyndham Winchester: Offers daily, a pool, and free self parking.
What is there to see and do in Winchester?
Spend some time experiencing the great outdoors at College Park and GRCHS Baseball Field. During your stay, check out sights such as Bluegrass Heritage Museum, Cassell Creek Golf Course, and Winchester Opera House. 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.

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