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.

Find Hotels with Bars in Winchester, KY

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Check availability on Winchester Hotels with Bars

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Winchester hotels with a bar

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

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 NT$3,625
NT$3,996 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Winchester
A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

2. Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,000 reviews)
"They have a really good Breakfast..."
United States
David
The price is NT$2,804
NT$3,092 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, (866 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is NT$2,600
NT$2,866 total
includes taxes & fees
Nov 11 - Nov 12
Baymont by Wyndham Winchester
A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

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, (614 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 NT$3,838
NT$4,231 total
includes taxes & fees
Dec 3 - Dec 4
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, (195 reviews)
"Well worth the money"
United States
Ronald
The price is NT$1,922
NT$2,119 total
includes taxes & fees
Nov 11 - Nov 12
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 NT$2,510
NT$2,766 total
includes taxes & fees
Dec 1 - Dec 2
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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Top Winchester Hotel Reviews

Elwood Hotel & Suites

Elwood Hotel & Suites

8/10 Good
"Cute boutique hotel. Friendly staff. Concrete floors in the suite needed a rug in the bedroom."
Michael 5-night trip
Posted 15 hours ago
Elwood Hotel & Suites

Frequently asked questions

Searching for hotels with bars in Winchester?
Winchester features 23 properties to choose from, and likely many will have a bar where you can enjoy drink after a day of exploring. While you're here, consider a visit to Bluegrass Heritage Museum and Cassell Creek Golf Course.
What are the best hotels with bars in Winchester?
Here are a few of the top hotels with bars in and around Winchester: Holiday Inn Express Lexington - Horse Park Area by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. Hyatt Regency Lexington: Resort with restaurant. Enjoy the bar, free parking, and seasonal outdoor pool. Marriott Lexington Griffin Gate Golf Resort & Spa: Hotel with 2 restaurants. Enjoy the 2 bars, free WiFi, and breakfast. The Manchester: Hotel with restaurant. Enjoy the bar, free WiFi, and room service. 21c Museum Hotel Lexington: Cabin with restaurant. Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Winchester?
To experience the area's highlights, consider visiting Fort Boonesborough State Park, Kentucky River, and Hamburg Pavilion, and then find a cozy spot for a nightcap. Other places to see include Bluegrass Heritage Museum and Cassell Creek Golf Course. Winchester is known for its restaurants.
When is the best time to visit Winchester?
Visiting local bars in Winchester is more fun in good weather. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
How can I get to Winchester and around the area?
You might want to make the most of these transportation choices in and around Winchester: Fly into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) away from the heart of the city. If you'd like to explore around the area, you may want to rent a car for your trip.

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