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Search Holiday Rentals in Winchester

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

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

Cabin in Slade

Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1,792 reviews)
"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."
United States
Kimberly
Natural Bridge State Resort Park
House (1 Bedroom) | Interior
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Cottage in Frenchburg

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
3.0 star property
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 2.574.068 ₫
6.888.259 ₫ total
includes taxes & fees
13 Jan - 14 Jan
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.
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Top Winchester Hotel Reviews

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

10/10 Excellent
"Great stay and the bed was extremely comfortable "
Kasey 1-night trip
Posted 1 day ago
Baymont by Wyndham Winchester

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?

College Park and GRCHS Baseball Field are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Cassell Creek Golf Course and Winchester Opera House 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.