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.

Best Resorts in Winchester

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Winchester resorts

Terrace/patio

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, (752 reviews)
"We really enjoyed our weekend stay and plan to return soon."
United States
Ed
$128 nightly
The price is $149
Jul 19 - Jul 20
Total with taxes and fees
Marriott Lexington Griffin Gate Golf Resort & Spa
WiFi, bed sheets

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

Climber's Cove - A Canvas Cabin in Red River Gorge
Stanton
$200 nightly
The price is $218
Jul 15 - Jul 16
Total with taxes and fees
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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"This hotel worked out very well for my friends and me. The room not spacious, but adequate. We found everything needed for the pull out couch within the room (nothing missing). The wifi worked fine. There was a small refrigerator and a microwave in the room. The only sink is the one in the bathroom. A second sink would be a significant improvement. The breakfast was generally good, although fruit was limited. The staff were helpful. It was easy to park very close to a door. The exercise room had only one working treadmill. This was OK only because I used it at an unpopular time. Having Cracker Barrel right next door is helpful for a meal without needing to drive anywhere."
Pauline 5-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Lexington North

Find out more about Winchester

Winchester Resorts information

Number of reviews
752
Accommodation
2 Resorts
Lowest Price
$149
Highest Price
$149

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 Lykins Park.
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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