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.

Winchester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchester vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. 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
9.8 out of 10, Exceptional, (11 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is AED 545
AED 1,116 total
includes taxes & fees
8 Aug - 9 Aug
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
A black leather sofa with a center console, a glass table, and two boxes on the table.

2. 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 AED 496
AED 1,085 total
includes taxes & fees
10 Aug - 11 Aug
The Winchester
Exterior

3. River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.8 out of 10, Good, (6 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 AED 657
AED 1,639 total
includes taxes & fees
9 Aug - 10 Aug
River Relaxation - Calm Riverfront Home in Winchester Kentucky
Smart TV, fireplace, books

4. 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, (112 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 traveler
The price is AED 378
AED 695 total
includes taxes & fees
9 Aug - 10 Aug
Unique Stay in a 1907 Log Cabin on The Kentucky River
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

5. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,985 reviews)
"Clean room and good continental breakfast."
United States
Jeff
The price is AED 334
AED 368 total
includes taxes & fees
20 Aug - 21 Aug
Natural Bridge State Resort Park
Exterior detail

6. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is AED 1,194
AED 1,788 total
includes taxes & fees
9 Aug - 10 Aug
Cabin in Kentucky Horse Country
Smart TV, fireplace, books

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, (75 reviews)
"Excellent stopover. "
United States
Robert W.
The price is AED 477
AED 895 total
includes taxes & fees
31 Aug - 1 Sep
1800’s Historical Log Cabin near I-75 Interstate
Coffee/tea maker, fridge, microwave, oven

8. Entire Home in Hamburg!

Entire Home in Hamburg!
Liberty Area
10.0 out of 10, Exceptional, (35 reviews)
"Very nice place. "
United States
Monte R.
The price is AED 643
AED 1,731 total
includes taxes & fees
13 Aug - 14 Aug
Entire Home in Hamburg!
Property grounds

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

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (87 reviews)
"Secluded cabin - we loved the quiet "
United States
Scot
The price is AED 397
AED 964 total
includes taxes & fees
16 Aug - 17 Aug
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Coffee/tea maker, fridge, microwave, oven

10. Cozy farmhouse family friendly with fire pit and grill, within hour to Keeneland

Cozy farmhouse family friendly with fire pit and grill, within hour to Keeneland
Paris
10.0 out of 10, Exceptional, (21 reviews)
"Such a peaceful, cozy place to stay. "
United States
Ninette W.
The price is AED 463
AED 1,162 total
includes taxes & fees
9 Aug - 10 Aug
Cozy farmhouse family friendly with fire pit and grill, within hour to Keeneland
Exterior

11. Hot Tub | Walkable | Patio | Fire Pit | Game Room

Hot Tub | Walkable | Patio | Fire Pit | Game Room
Hollywood - Mt. Vernon
10.0 out of 10, Exceptional, (189 reviews)
"Great spot! Twin bed couch as far as we could tell, but the amenities were wonderful, space was thoughtfully curated, and host was thoughtful. Really enjoyed this stay!"
United States
Yancey S.
The price is AED 848
AED 2,154 total
includes taxes & fees
16 Aug - 17 Aug
Hot Tub | Walkable | Patio | Fire Pit | Game Room
Coffee/tea maker, fridge, microwave, oven

12. Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Richmond
9.8 out of 10, Exceptional, (90 reviews)
"Everything was fantastic!!"
United States
Leah Anne G.
The price is AED 389
AED 806 total
includes taxes & fees
9 Aug - 10 Aug
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Exterior

13. Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms

Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
Downtown Lexington
10.0 out of 10, Exceptional, (55 reviews)
"Great location, safe and plenty of space. Communication with host was outstanding. Would definitely stay again."
United States
Andy
The price is AED 1,062
AED 1,799 total
includes taxes & fees
9 Aug - 10 Aug
Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
Smart TV

14. My Old Kentucky Home

My Old Kentucky Home
Lexington
9.8 out of 10, Exceptional, (31 reviews)
"Great place for a nice weekend visit."
United States
brian g.
The price is AED 286
AED 887 total
includes taxes & fees
11 Aug - 12 Aug
My Old Kentucky Home
Terrace/patio

15. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (86 reviews)
"Our second visit here. Host very responsive, location great and very clean. Would recommend to anyone looking to visit the area."
United States
Robert C.
The price is AED 445
AED 652 total
includes taxes & fees
16 Aug - 17 Aug
Mountain Memories Cabin
Terrace/patio

16. Relaxing Hot Tub | S’mores Fire Pit | Garage

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.4 out of 10, Exceptional, (54 reviews)
"We thoroughly enjoyed our stay! Dalton was easy to communicate with, gave clear guidance for check-in and check-out procedures, and offered a lovely home to relax in. If back in the area we would absolutely stay here again!"
United States
Tara G.
The price is AED 382
AED 1,034 total
includes taxes & fees
10 Aug - 11 Aug
Relaxing Hot Tub | S’mores Fire Pit | Garage
TV, fireplace

17. Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge
Stanton
10.0 out of 10, Exceptional, (8 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
The price is AED 346
AED 666 total
includes taxes & fees
9 Aug - 10 Aug
Dappled Grey Cabin with hot tub at Red River Gorge
Terrace/patio

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

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (55 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is AED 625
AED 782 total
includes taxes & fees
10 Aug - 11 Aug
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Interior

19. Bourbon Condo Downtown Lexington

Bourbon Condo Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (16 reviews)
"We only stayed for a quick night but the apartment was really cute, clean, and right off main street. The beds were comfortable too."
United States
Michele G.
The price is AED 505
AED 973 total
includes taxes & fees
9 Aug - 10 Aug
Bourbon Condo Downtown Lexington
Terrace/patio

20. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (41 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is AED 430
AED 636 total
includes taxes & fees
9 Aug - 10 Aug
Mountaintop Cottage
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 6 hours ago
Holiday Inn Lexington - Hamburg by IHG

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, we offer vacation rentals close to top points of interest in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Our travelers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffeehouses and shopping during your trip.

What are some of the best vacation home rentals that Winchester has to offer?

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.: Visitors like this Winchester vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge to make your meal-planning easier.

How many vacation rentals are there in Winchester?

Expedia has 7 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Wiseman Park and Winchester Traveling Trail are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Winchester Opera House and Clark County Courthouse are other places to visit while you're in town.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.