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Best Resorts in Winchester

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 1 Resorts in Winchester with updated reviews, rates, and availability.

Marriott Lexington Griffin Gate Golf Resort & Spa
Terrace/patio

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 star property
8.6 out of 10, Excellent, (418)
"Its beufitil country hotel, Many ammenities, golf course, traditions. But. Downtown is where goodreataurant are.! People is honest and kind "
The price is $165
includes taxes & fees
$137 per night
May 26 - May 27
Marriott Lexington Griffin Gate Golf Resort & Spa
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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Other property types in Winchester

Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1536)
"This hotel is a mountain lodge. It was very comfortable. Ok on cleanliness. The balcony of the room was like to were in the middle of the forest, very relaxing to sit and have a cocktail or coffee. I loved the fact that it was very close to hiking trails to the natural bridge. You can just walk out your door from the hemlock lodge and the trails are right in the parking lot behind the lodge. The surrounding area is absolutely beautiful. The breakfast was good also. I would definitely stay here...
The price is $133
includes taxes & fees
$121 per night
May 13 - May 14
Natural Bridge State Resort Park
Tranquil Getaway in the Woods ~ Sunset Ridge
Terrace/patio

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (53)
"The perfect cabin for a weekend get away. Clean, cute, and cozy. "
The price is $149
includes taxes & fees
$135 per night
May 4 - May 5
Tranquil Getaway in the Woods ~ Sunset Ridge
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Exterior

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (65)
"Beautiful cabin w/an amazing view and bonus hot tub!"
The price is $219
includes taxes & fees
$198 per night
May 1 - May 2
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
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.

Frequently asked questions

What can I expect from a resort vacation in Winchester?
Longing for a relaxing getaway? Treat yourself to the comforts of a resort, where you can find everything you need for your stay from convenient dining options to activities and entertainment. There are 8 resorts in the area, offering you a variety of options that might have the luxurious suites or fun activities you’re looking for.
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 Cassell Creek Golf Course and College 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.