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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winchester vacation rentals

Cabin, Private Bathroom (The Pond Cabin) | Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is NT$7,693
NT$14,699 total
includes taxes & fees
Jul 13 - Jul 14
The Pond Cabin
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (43 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back "
United States
Varnell
The price is NT$3,476
NT$3,904 total
includes taxes & fees
Jul 13 - Jul 14
Roadhaven1830
Cabin, 1 Queen Bed, Mountain View | Pillowtop beds, free WiFi, bed sheets

Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (16 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
United States
Nebojsa
The price is NT$4,571
NT$5,165 total
includes taxes & fees
Jul 19 - Jul 20
Canal Cabins
House (3 Bedrooms) | Interior

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
3.0 star property
Harpers Ferry
The price is NT$4,539
NT$11,072 total
includes taxes & fees
Aug 12 - Aug 13
5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
7.0 out of 10, Good, (10 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is NT$4,176
NT$7,968 total
includes taxes & fees
Jul 13 - Jul 14
2-Bedroom cabin Hot tub Fireplace PS5
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"Very nice, love the wood ceilings. Only complaint is that the walls are pretty thin and can hear conversations in attached rooms."
Beth 1-night trip
Posted 5 hours ago
Quality Inn Winchester

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

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

How many vacation rentals will I find in Winchester?

Choose from 14 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of family-friendly sights, whereas cultural attractions include Winchester Little 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 vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.