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 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Winchester vacation rentals

Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,969 reviews)
"Outdated cottage in need of repair."
United States
Shannon
The price is NT$3,092
NT$3,408 total
includes taxes & fees
Aug 23 - Aug 24
Natural Bridge State Resort Park
House | 6 bedrooms

Beautiful House in Nicholasville

Beautiful House in Nicholasville
2.0 star property
Nicholasville
The price is NT$29,108
NT$42,267 total
includes taxes & fees
Aug 3 - Aug 4
Beautiful House in Nicholasville
House (1 Bedroom) | Interior

Plum Crazy: Frenchburg Cabin on 1 Acre

Plum Crazy: Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveler
The price is NT$4,572
NT$9,370 total
includes taxes & fees
Jul 26 - Jul 27
Plum Crazy: Frenchburg Cabin on 1 Acre
House (0 Bedroom) | Interior

Retro Studio: Romantic Getaway in Frenchburg

Retro Studio: Romantic Getaway in Frenchburg
4.0 star property
Frenchburg
6.0 out of 10, (1 review)
"Stay was okay. Building was clean and everything worked well. Location was much further from red river gorge than expected, about 45 minutes to 1 hour 15 minutes one way to a trail. Bed was very hard. Hot tub was nice. Overall, decent if you dont mind the sleeping conditions and the drive but for us it wasnt worth the cost "
United States
Michael
The price is NT$5,026
NT$9,870 total
includes taxes & fees
Jul 26 - Jul 27
Retro Studio: Romantic Getaway in Frenchburg
House (2 Bedrooms) | Interior

Ridgefolk Retreats! Set of 2 Cabins in Frenchburg

Ridgefolk Retreats! Set of 2 Cabins in Frenchburg
3.0 star property
Frenchburg
The price is NT$10,431
NT$20,237 total
includes taxes & fees
Aug 17 - Aug 18
Ridgefolk Retreats! Set of 2 Cabins in Frenchburg
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Very close to Rupp arena"
Michael 3-night trip
Posted 3 hours ago
Hyatt Regency Lexington

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.

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 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.