Search Holiday Rentals in Winchester

  • 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
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winchester holiday 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, (1,849 reviews)
"What a great staff Very clean, friendly hotel Def will stay again"
United States
Loreli
The price is 2.748.370 ₫
3.029.660 ₫ total
includes taxes & fees
3 May - 4 May
Natural Bridge State Resort Park
House (1 Bedroom) | Interior

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful 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 traveller
The price is 2.581.124 ₫
7.229.781 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
House, 5 Bedrooms | Living room

Andrea Abode 5 Bedroom Home by RedAwning

Andrea Abode 5 Bedroom Home by RedAwning
3.5 star property
Open Gates
10.0 out of 10, Exceptional, (1 review)
"Large home. Loved the game room "
United States
Marian
The price is 7.882.927 ₫
28.962.287 ₫ total
includes taxes & fees
30 Apr - 1 May
Andrea Abode 5 Bedroom Home by RedAwning
Apartment (0 Bedroom) | Interior

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg

Hot Tub & Fire Pit: Romantic Getaway in Frenchburg
3.5 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
Hot Tub & Fire Pit: Romantic Getaway 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.
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

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

10/10 Excellent
"Great place"
Melissa 3-night trip
Posted 5 hours ago
Origin Lexington a Wyndham Hotel

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffee shops and shopping during your trip.

How many holiday rentals are there in Winchester?

Expedia has 6 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Winchester Traveling Trail and Lykins 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.