Winchester, KY

Travel Guide

Photo by Hyelsinta
Photo by Hyelsinta
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
The price is SAR 605 per night from Jun 29 to Jun 30
SAR 605
SAR 767 total
29 Jun - 30 Jun
includes taxes & fees
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. ...
9.4/10 Exceptional! (864 reviews)
"Very nice, hotel and rooms. It would be easier if parking and breakfast were included in the price of the stay. Would stay again if in Lexington."

Reviewed on 5 June 2025

The Manchester
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
The price is SAR 224 per night from Jul 6 to Jul 7
SAR 224
SAR 260 total
6 Jul - 7 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,195 reviews)
Convenient location and clean!
"Surprisingly well. Very nice and helpful reception from front desk. When I did walk in the room, it was dated but the sheets looked and felt clean, towels were clean, and the bathroom was clean. Very important to me."

Reviewed on 4 June 2025

GuestHouse Lexington
DoubleTree Suites by Hilton Hotel Lexington
DoubleTree Suites by Hilton Hotel Lexington
4 out of 5
2601 Richmond Rd, Lexington, KY
The price is SAR 407 per night from Jun 29 to Jun 30
SAR 407
SAR 473 total
29 Jun - 30 Jun
includes taxes & fees
Stay at this hotel in Lexington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (1,003 reviews)
"Great service!"

Reviewed on 2 June 2025

DoubleTree Suites by Hilton Hotel Lexington
See all 1,131 properties in 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.
Natural Bridge State Resort Park
Natural Bridge State Resort Park
3.5 out of 5
2135 Natural Bridge Road, Slade, KY
Stay at this 3.5-star cabin in Slade. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (1,583 reviews)
"It wasn’t a bad place to stay for the price. Especially if you like hiking, and the outdoors But the cabin could use a few updates. And we had gone out for the day for a hike, and came back to a whole lot of mouse droppings, and a half eaten muffin. And it wasn’t me who ate the muffin. lol. I get ..."

Reviewed on 6 June 2025

Natural Bridge State Resort Park
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Stanton
Stay at this cabin in Stanton. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Red River Gorge and Natural Bridge State Park ...
9.4/10 Exceptional! (114 reviews)
Super cute!
"We enjoyed the cabin it was a super cute place. My only complaint was when we arrived the couch was torn up and there was cookies all over it. Other than that it was a great place, close to everything you want to experience"

Reviewed on 26 March 2025

Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Stanton
Stay at this cabin in Stanton. Enjoy laundry facilities, concierge services, and patios. Popular attractions Natural Bridge State Park and Kentucky Reptile Zoo ...
9.6/10 Exceptional! (144 reviews)
Quiet retreat
"The cabin was clean and in good order. Everything we needed was there . We only needed to bring ourselves and the food . The hot tub was enjoyed in the evenings after exploring the gorge all day . We hiked in three different areas of the park and came back to peace and quiet . I counted 4 cars go ..."

Reviewed on 30 April 2025

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
See all properties in 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.

Popular places to visit

Kentucky Horse Park showing land animals

Kentucky Horse Park

4.5/5(328 reviews)

Explore Kentucky Horse Park, a favorite green space in Lexington, and also enjoy the area's horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
In a hores eye #2

University of Kentucky

4.5/5(384 reviews)

Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
The Kentucky Castle

The Kentucky Castle

4.5/5(24 reviews)

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle
It's beginning to look a lot like Christmas.

Fayette Mall

4.5/5(321 reviews)

You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.

Fayette Mall
Recreation of the fort Daniel Boone settled. Informative and friendly docents.

Fort Boonesborough State Park

4.5/5(38 reviews)

Find out about the history of Richmond when you spend time at Fort Boonesborough State Park. While in this family-friendly area, you can savor the top-notch restaurants.

Fort Boonesborough State Park
The fountain

Eastern Kentucky University

4.5/5(170 reviews)

Enjoy the collegiate vibe when you visit Eastern Kentucky University, during your travels in Richmond. While in this family-friendly area, you can savor the top-notch restaurants.

Eastern Kentucky University

Reviews of Winchester

4
Top Destination
5 - Excellent
23
5 - Excellent 27%
4 - Good
44
4 - Good 51%
3 - Okay
16
3 - Okay 19%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
3
1 - Terrible 3%

5/5 - Excellent

Verified traveler

Pretty small town. quiet on sunday. The Italian restaurant La Trattoria was really nice. The chef sat by me and happened to adjust the entree for me. A pretty lady talked about travel a while and made me feel welcome. maybe was the owner.

5/5 - Excellent

Verified traveler

The rooms and beds are very comfortable and flooring is attractive and updated. Hairdryers are available upon request. Breakfast options were the best! Scrambled eggs, sausage, bacon, fruit, waffles, cereal, pastries, yogurt, with flavored creamers

1/5 - Terrible

Verified traveler

This Place is a SHAM!!! DON'T STAY HERE, it's Dirty and the amenities listed are not working or are a lie all together. very poor excuse was given 'BEING RENOVATED' thats a lie and it should be listed in all the travel apps as such.

4/5 - Good

Verified traveler

No food or shopping available in the surrounding area, where we stayed.

3/5 - Okay

Verified traveler

Never staying at another red roof inn.

4/5 - Good

Verified traveler

Loed Hall's on the River