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
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winchester vacation rentals

Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,829 reviews)
"What a great staff Very clean, friendly hotel Def will stay again"
United States
Loreli
The price is P6,319
P6,966 total
includes taxes & fees
Apr 12 - Apr 13
Natural Bridge State Resort Park
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 traveler
The price is P5,934
P15,881 total
includes taxes & fees
Apr 5 - Apr 6
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
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

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Nice place to stay in Lexington. Loved the horse themed decor. Staff was friendly. They provide a hot breakfast. Rooms were clean and updated, comfortable beds. Quiet."
Candice 1-night trip
Posted 1 hour ago
GuestHouse 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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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 6 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Winchester Traveling Trail 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.