A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday rentals

Exterior

1. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is S$607
includes taxes & fees
29 Sept - 30 Sept
The Pond Cabin
Lobby

2. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (51 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is S$186
includes taxes & fees
12 Oct - 13 Oct
Roadhaven1830
Interior

3. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
3.0 star property
Luray
The price is S$427
includes taxes & fees
22 Sept - 23 Sept
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
Room

4. Schilling House

Schilling House
3.0 star property
Bolivar
The price is S$430
includes taxes & fees
29 Sept - 30 Sept
Schilling House
Interior

5. 2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
6.4 out of 10, (12 reviews)
"This place was wonderful. When have stayed at 4 different cabins like this and this was our favorite. The place was cozy and clean. The pantry was well stocked. The fire pit even had a wood fire prepared. The owners were really nice and communicated well. The facilities at the woods were included We live very the location and the hot tub Highly recommend"
United States
Christopher
The price is S$347
includes taxes & fees
22 Sept - 23 Sept
2-Bedroom cabin Hot tub Fireplace PS5
Pillow-top beds, free WiFi, bed sheets

6. Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (17 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
United States
Nebojsa
The price is S$197
includes taxes & fees
2 Oct - 3 Oct
Canal Cabins
Interior

7. 'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
'thomson Farm' Classic Home < 10 Mi to Vineyards!
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Nice area. Very clean. Delicious and hot breakfast."
Rebekah 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Winchester, VA

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

How many holiday rentals will I find in Winchester?

Choose from 15 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.