Search Resort Hotels in Winchester from CA $144

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Winchester resorts

A fire pit with seating and umbrellas in an outdoor area.

1. Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa
4.5 star property
Lexington
8.4 out of 10, Very good, (890 reviews)
"Hotel was very beautiful and staff was very accommodating. The hotel car was a big bonus!"
United States
KELVIN
The price is CA $145
CA $197 total
includes taxes & fees
Nov 15 - Nov 16
Marriott Lexington Griffin Gate Golf Resort & Spa
A tent-style bedroom with a large bed, a small table with a plant, and a view of trees through the window.

2. Climber's Cove - A Canvas Cabin in Red River Gorge

Climber's Cove - A Canvas Cabin in Red River Gorge
Stanton
The price is CA $171
CA $293 total
includes taxes & fees
Nov 15 - Nov 16
Climber's Cove - A Canvas Cabin in Red River Gorge
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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Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

See all hotels in Winchester
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.

Frequently Asked Questions

What can I expect from a resort vacation in Winchester?

Longing for a relaxing escape? You deserve the comforts and luxuries of a resort, where you can find everything you need for your vacation from convenient dining options to activities and shopping. Browse the resorts in the area and discover the one that's best for you, whether you picture yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.

What's the best resort for my stay in Winchester?

Our top-rated resort near Winchester: Marriott Lexington Griffin Gate Golf Resort & Spa - Luxury resort. 18.1 mi (29.1 km) from Winchester. Features a golf course, a full-service spa, and a seasonal outdoor pool. Guests love the pool.

What can I do in Winchester?

Check out the interesting exhibits at Bluegrass Heritage Museum, or grab your golf clubs for a game at Cassell Creek Golf Course. Additional attractions in the area include Winchester Opera House and Clark County Courthouse.

What's the seasonal weather like in Winchester?

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 the best way to get to 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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