Photo by Jeff Rogers /Lexington Convention and Visitors Bureau

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Top cities in Clark County

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.
Vacation Rentals

Winchester

Winchester

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Clark County holiday rentals

A two-story house with a porch and a front yard.

1. Charming Victorian Apartment | Downtown Winchester

Charming Victorian Apartment | Downtown Winchester
Winchester
The price is £281
includes taxes & fees
16 Nov - 17 Nov
Charming Victorian Apartment | Downtown Winchester
A bedroom with a bed, nightstands, and a dresser.

2. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.6 out of 10, Exceptional, (14 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is £208
includes taxes & fees
16 Nov - 17 Nov
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A two-story wooden cabin with a balcony, surrounded by trees.

3. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
8.0 out of 10, Very good, (8 reviews)
"Good communication, great location and peaceful! Back deck to River does need a little work but it was overall a good stay! "
United States
Polly H.
The price is £260
includes taxes & fees
16 Nov - 17 Nov
River Relaxation - Calm Riverfront Home in Winchester Kentucky
A two-story house with a covered porch, a brick exterior, and a small garden area with shrubs.

4. The Winchester

The Winchester
Winchester
8.6 out of 10, Excellent, (11 reviews)
"The house was clean and had all amenities needed. Love the location and was adorable. Wish I could have stayed longer. Love that there is a park across the street and the neighbors were very friendly"
United States
Gina
The price is £212
includes taxes & fees
23 Nov - 24 Nov
The Winchester
A wooden cabin with a porch, a dining area with a table and chairs, and a stack of firewood.

5. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,140 reviews)
"Love staying here, such easy access to the Gorge and Natural Bridge. Always convenient and easy to deal with. Always a place I keep in mind when I’m staying in the area."
United States
Logan
The price is £46
includes taxes & fees
10 Dec - 11 Dec
Natural Bridge State Resort Park
A log cabin interior with a wooden desk, leather armchair, and a patterned rug.

6. Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (114 reviews)
"Cabin was very unique, and charming. Had everything we needed. Steps a little wonky but easy to get through. Would definitely stay again. "
United States
Anonymous traveller
The price is £140
includes taxes & fees
23 Nov - 24 Nov
Unique Stay in a 1907 Log Cabin on The Kentucky River
A log cabin interior with a sofa, a coffee table, a fireplace, and a staircase leading to another room.

7. 1800’s Historical Log Cabin near I-75 Interstate

1800’s Historical Log Cabin near I-75 Interstate
Lexington
9.4 out of 10, Exceptional, (86 reviews)
"Great location and home for our 10 year anniversary"
United States
Christopher S.
The price is £193
includes taxes & fees
16 Nov - 17 Nov
1800’s Historical Log Cabin near I-75 Interstate
A cabin with a deck, a fire pit, and string lights in a forest setting.

8. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (134 reviews)
"It was a great cozy place for a weekend for me and my sister. It had everything we needed and we especially loved having the window bed! Would definitely consider staying here again."
United States
Anonymous traveller
The price is £155
includes taxes & fees
15 Nov - 16 Nov
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
A living room with a beige sofa, a large plant, a wall mural, a door with a star decoration, and a black entertainment unit.

9. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very good, (25 reviews)
"This is definitely an older home, but it was clean and comfortable and the Dolly memorabilia is amazing!"
United States
Glenda
The price is £89
includes taxes & fees
15 Nov - 16 Nov
Cozy, Bright Home in Historic Downtown
A wooden deck with a chair and a table, surrounded by greenery and a 'Welcome' sign.

10. The Towner : Sleeps 4 • Near RRG • Walk to Town

The Towner : Sleeps 4 • Near RRG • Walk to Town
Stanton
9.8 out of 10, Exceptional, (52 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is £164
includes taxes & fees
15 Nov - 16 Nov
The Towner : Sleeps 4 • Near RRG • Walk to Town
A hot tub in a wooden outdoor area with a view of trees and a dirt path.

11. Larkspur Cabin with Hot Tub near Red River Gorge

Larkspur Cabin with Hot Tub near Red River Gorge
Stanton
9.8 out of 10, Exceptional, (11 reviews)
"My wife and I had a very relaxing get away. Lovely place for a couple."
United States
Anonymous traveller
The price is £124
includes taxes & fees
17 Nov - 18 Nov
Larkspur Cabin with Hot Tub near Red River Gorge
A wooden porch with two chairs and a ceiling fan.

12. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (100 reviews)
"Great little place , clean and comfortable quiet nice place to just relax for a few days and take in the fresh air"
United States
Jason B.
The price is £126
includes taxes & fees
24 Nov - 25 Nov
Mountain Memories Cabin
A wooden deck with a bar area, a seating arrangement, and a grill.

13. Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
Irvine
10.0 out of 10, Exceptional, (22 reviews)
"Loved this cabin was in such a beautiful location will definitely stay there again…."
United States
Shari L.
The price is £156
includes taxes & fees
15 Nov - 16 Nov
Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
A covered outdoor patio with a grill and seating area.

14. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (51 reviews)
"House is great, very comfortable and clean. Owners are very friendly and responsive."
United States
Mike P.
The price is £129
includes taxes & fees
17 Nov - 18 Nov
Mountaintop Cottage
A modern living room with a glass coffee table, leather armchair, dining area with chairs, and a chandelier.

15. Luxury on Main / South & Downtown Hideaway

Luxury on Main / South & Downtown Hideaway
Richmond
10.0 out of 10, Exceptional, (58 reviews)
"Adorable place. Very clean. Great location. Close to many restaurants and shops. Loved it."
United States
Jordan B.
The price is £132
includes taxes & fees
13 Nov - 14 Nov
Luxury on Main / South & Downtown Hideaway
A wooden cabin with a porch, surrounded by trees and a gravel driveway.

16. Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
9.8 out of 10, Exceptional, (102 reviews)
"A wonderful place to stay!"
United States
Deb H.
The price is £209
includes taxes & fees
15 Nov - 16 Nov
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
A hot tub in a forested area with Adirondack chairs, a wooden deck, and a red building with shipping containers.

17. Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods

Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
Stanton
10.0 out of 10, Exceptional, (344 reviews)
"great secluded property with everything we needed for a great weekend. Hot Tub was nice after a day of hiking."
United States
Kenneth
The price is £221
includes taxes & fees
19 Nov - 20 Nov
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
A wooden deck with two chairs and a table, overlooking a pond and a metal-roofed structure.

18. Tiny Cabin At The Pond

Tiny Cabin At The Pond
Stanton
9.6 out of 10, Exceptional, (32 reviews)
"From booking to check out the property and Martin were fantastic. I wish we could've stayed longer."
United States
Justin A.
The price is £178
includes taxes & fees
15 Nov - 16 Nov
Tiny Cabin At The Pond
A hot tub with a fire pit in a forested area.

19. Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape

Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
Stanton
10.0 out of 10, Exceptional, (49 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is £195
includes taxes & fees
16 Nov - 17 Nov
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
A wooden deck with rocking chairs and a table, leading to a glass door.

20. Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (70 reviews)
"Best cabin I have ever stayed at."
United States
Richard D.
The price is £163
includes taxes & fees
16 Nov - 17 Nov
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
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 Clark County Hotel Reviews

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
Winchester

10/10 Excellent

The hotel represents excellent value for money. Everything is very clean and the staff very helpful.
United Kingdom
Roy
Reviewed April 28, 2026
Best Western Winchester Hotel

Find out more about Clark County

Everything you need to know about Clark County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Clark County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Clark County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Clark County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Clark County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Clark County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Clark County holiday rentals we have selected for you start as low as £46 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Clark County rentals

At Expedia, we put the best Clark County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Clark County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Clark County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Clark County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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