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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

A black leather sofa with a center console, a glass table, and two boxes on the table.

1. 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 ￥23,604
￥48,276 total
includes taxes & fees
Aug 30 - Aug 31
The Winchester
Coffee/tea maker, fridge, microwave, oven

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
9.8 out of 10, Exceptional, (12 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is ￥23,604
￥49,678 total
includes taxes & fees
Aug 26 - Aug 27
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

3. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,011 reviews)
"Friendly staff and good view."
United States
LE VAN
The price is ￥15,156
￥16,707 total
includes taxes & fees
Aug 31 - Sep 1
Natural Bridge State Resort Park
Dining

4. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
10.0 out of 10, Exceptional, (347 reviews)
"Felt very comfortable during our stay,plenty of space for us both."
United States
Anonymous traveler
The price is ￥9,694
￥10,663 total
includes taxes & fees
Aug 26 - Aug 27
2 Full Beds | Non-Smoking, Micfridge
Exterior

5. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.6 out of 10, Exceptional, (14 reviews)
"We loved staying at this super lovely little house! It was perfect for two people, everything we needed and great location! If we ever plan a trip to Lexington- this is absolutely where we will stay!"
Canada
Renae
The price is ￥8,154
￥31,788 total
includes taxes & fees
Aug 30 - Aug 31
Cozy 1-bedroom in Lexington
Property grounds

6. Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very Good, (23 reviews)
"Great stay as usual. Owners are super friendly & helpful. This was our 3rd time staying as we've made this our regular when visiting family in the area."
United States
Brittany K.
The price is ￥10,014
￥19,801 total
includes taxes & fees
Aug 30 - Aug 31
Cozy, Bright Home in Historic Downtown
Smart TV, fireplace, books

7. 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 ￥16,372
￥30,073 total
includes taxes & fees
Aug 27 - Aug 28
Unique Stay in a 1907 Log Cabin on The Kentucky River
Property grounds

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, (122 reviews)
"great place!"
United States
Ava G.
The price is ￥14,019
￥30,699 total
includes taxes & fees
Aug 30 - Aug 31
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Smart TV, fireplace, books

9. 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)
"It was really great staying in a historical home. It was clean and very comfortable."
United States
Nancy L.
The price is ￥19,727
￥38,593 total
includes taxes & fees
Aug 31 - Sep 1
1800’s Historical Log Cabin near I-75 Interstate
Property grounds

10. 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 traveler
The price is ￥14,989
￥27,066 total
includes taxes & fees
Aug 30 - Aug 31
Larkspur Cabin with Hot Tub near Red River Gorge
Outdoor dining

11. Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Downtown Lexington
10.0 out of 10, Exceptional, (38 reviews)
"Great spot, great location, great host."
United States
Jill
The price is ￥16,610
￥24,813 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Dining

12. Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (54 reviews)
"Clean, well stocked and comfortable. I always enjoy my stay here. "
United States
Robert T.
The price is ￥15,100
￥28,913 total
includes taxes & fees
Aug 30 - Aug 31
Luxury on Main / South
TV

13. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Lexington
8.8 out of 10, Excellent, (16 reviews)
"The condo was beautiful and very clean and everything we needed from dishes and kitchen items to laundry, facilities, and soap and accessories. We enjoyed this place and will happily stay again."
United States
Sylvia B.
The price is ￥15,100
￥27,400 total
includes taxes & fees
Aug 30 - Aug 31
This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Lobby

14. Graffiti Art Haus - Walk to Central Bank Arena

Graffiti Art Haus - Walk to Central Bank Arena
Downtown Lexington
10.0 out of 10, Exceptional, (56 reviews)
"Awesome property in great location, host was very helpful, highly recommend!"
United States
Kyle B.
The price is ￥11,683
￥31,693 total
includes taxes & fees
Aug 30 - Aug 31
Graffiti Art Haus - Walk to Central Bank Arena
Coffee/tea maker, fridge, microwave, oven

15. 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 ￥17,010
￥35,286 total
includes taxes & fees
Aug 26 - Aug 27
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Living area

16. 3 Miles Hollerwood/ATV Parking/Mountain Views

3 Miles Hollerwood/ATV Parking/Mountain Views
Zoe
9.8 out of 10, Exceptional, (9 reviews)
"Remote and nice location with plenty of room. "
United States
Keith P.
The price is ￥10,815
￥39,784 total
includes taxes & fees
Aug 26 - Aug 27
3 Miles Hollerwood/ATV Parking/Mountain Views
Property grounds

17. Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
Stanton
9.4 out of 10, Exceptional, (21 reviews)
"Super enjoyable stay! My dog and I loved it!! Will be visiting again!"
United States
Ally W.
The price is ￥9,424
￥20,903 total
includes taxes & fees
Aug 26 - Aug 27
Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
TV

18. This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Lexington
8.6 out of 10, Excellent, (55 reviews)
"Great little house for a stay over!"
United States
Aura S.
The price is ￥13,352
￥30,312 total
includes taxes & fees
Sep 1 - Sep 2
This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
Interior

19. Luxurious 1-bedroom with Free Parking

Luxurious 1-bedroom with Free Parking
Lexington
9.8 out of 10, Exceptional, (75 reviews)
"It was perfect for a couple. We were there for a wedding and it was a great location."
United States
Deb A.
The price is ￥10,309
￥34,125 total
includes taxes & fees
Aug 31 - Sep 1
Luxurious 1-bedroom with Free Parking
Exterior

20. Luxe Home Downtown - Sleeps 6. Off-street parking

Luxe Home Downtown - Sleeps 6. Off-street parking
Northside District
9.6 out of 10, Exceptional, (30 reviews)
"Great house, clean and comfortable"
United States
Tim M.
The price is ￥15,021
￥40,529 total
includes taxes & fees
Aug 27 - Aug 28
Luxe Home Downtown - Sleeps 6. Off-street parking
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
"The breakfast was much better than the standard for this level hotei"
Cheryl 1-night trip
Posted 5 hours ago
Holiday Inn Express Lexington - Horse Park Area by IHG

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

Renovated train station on thoroughbred horse farm.: Visitors like this Winchester vacation home rental. It is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Winchester?

Expedia has 8 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Wiseman Park and College Park 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.