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

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Check prices for these dates

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

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.
$275 nightly
The price is $303
Aug 6 - Aug 7
Total with taxes and fees
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
$268 nightly
The price is $295
Aug 10 - Aug 11
Total with taxes and fees
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.
$413 nightly
The price is $455
Aug 9 - Aug 10
Total with taxes and fees
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
$163 nightly
The price is $189
Aug 9 - Aug 10
Total with taxes and fees
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, (1,983 reviews)
"Clean room and good continental breakfast."
United States
Jeff
$101 nightly
The price is $111
Aug 20 - Aug 21
Total with taxes and fees
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.
$450 nightly
The price is $489
Aug 6 - Aug 7
Total with taxes and fees
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.
$210 nightly
The price is $244
Aug 10 - Aug 11
Total with taxes and fees
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.
$409 nightly
The price is $475
Aug 12 - Aug 13
Total with taxes and fees
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
$238 nightly
The price is $262
Aug 16 - Aug 17
Total with taxes and fees
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.
$287 nightly
The price is $316
Aug 9 - Aug 10
Total with taxes and fees
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.
$510 nightly
The price is $587
Aug 16 - Aug 17
Total with taxes and fees
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.
$206 nightly
The price is $224
Aug 6 - Aug 7
Total with taxes and fees
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
$422 nightly
The price is $490
Aug 9 - Aug 10
Total with taxes and fees
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.
$208 nightly
The price is $241
Aug 11 - Aug 12
Total with taxes and fees
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.
$161 nightly
The price is $178
Aug 16 - Aug 17
Total with taxes and fees
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.
$222 nightly
The price is $256
Aug 6 - Aug 7
Total with taxes and fees
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
$222 nightly
The price is $228
Aug 9 - Aug 10
Total with taxes and fees
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, (54 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
$193 nightly
The price is $213
Aug 10 - Aug 11
Total with taxes and fees
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.
$233 nightly
The price is $265
Aug 6 - Aug 7
Total with taxes and fees
Bourbon Condo Downtown Lexington
Terrace/patio

20. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (40 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
$157 nightly
The price is $173
Aug 9 - Aug 10
Total with taxes and fees
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.
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Top Winchester Hotel Reviews

Holiday Inn Express Lexington - Horse Park Area by IHG

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent
"Amazing, clean, and great staff"
Kayli 1-night trip
Posted 17 hours ago
Holiday Inn Express Lexington - Horse Park Area by IHG

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $66 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 Winchester 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 Winchester vacation.

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

Explore a world of travel with Expedia

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.