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.

Search Resort Hotels in Winchester from CA $217

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Winchester resorts

Terrace/patio

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, (793 reviews)
"I enjoyed the quiet location, lovely property, clean rooms, comfortable beds, and friendly staff!"
United States
Wendy
The price is CA $163
CA $217 total
includes taxes & fees
Sep 6 - Sep 7
Marriott Lexington Griffin Gate Golf Resort & Spa
1 bedroom, WiFi, bed sheets

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 $170
CA $307 total
includes taxes & fees
Aug 11 - Aug 12
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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Top Winchester Hotel Reviews

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

10/10 Excellent
"Wonderful place to stay! Extremely helpful staff. Quiet...there was a volleyball tournament that weekend where the hotel was FULL! And It was still quite. It is very clean. The bed was super comfortable. We didn't get the breakfast for a fee. Overall, great place to stay and we will make this our hotel of choice when in Lexington."
Crystal 2-night trip
Posted less than an hour ago
Holiday Inn Lexington - Hamburg by IHG

Find out more about Winchester

Winchester Resorts information

Number of reviews
793
Accommodation
2 Resorts
Lowest Price
CA $217
Highest Price
CA $307

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 Southwind Golf Course. Additional attractions in the area include Wiseman Park and Winchester Traveling Trail.
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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