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.

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Check availability on Winchester Luxury Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Winchester luxury hotels

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 AED 372
AED 410 total
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn Winchester
A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

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 AED 331
AED 365 total
includes taxes & fees
4 Nov - 5 Nov
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, (864 reviews)
"Room was clean beds were comfortable"
United States
Ronald
The price is AED 293
AED 323 total
includes taxes & fees
8 Nov - 9 Nov
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, (613 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 AED 419
AED 462 total
includes taxes & fees
28 Nov - 29 Nov
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, (193 reviews)
"Well worth the money"
United States
Ronald
The price is AED 204
AED 225 total
includes taxes & fees
13 Nov - 14 Nov
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 AED 285
AED 314 total
includes taxes & fees
28 Nov - 29 Nov
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

10/10 Excellent
"The room was awesome, the staff friendly, and the restaurant was super delicious"
Kevin 3-night trip
Posted less than an hour ago
Elwood Hotel & Suites

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Winchester?
Use Expedia to help you arrange a flight to Blue Grass Airport (LEX) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winchester offers. During your visit, you might want to enjoy the restaurants which Winchester is known for.
When can I expect good weather in Winchester?
Planning for the weather is an important factor for making your trip to Winchester a success, especially when you're splurging. 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.
What's there to see and do in Winchester?
Experience Winchester and visit Bluegrass Heritage Museum, Cassell Creek Golf Course, and Winchester Opera House. If you have extra time while you're in the area, you might want to see Clark County Courthouse and College Park.

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