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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester vacation rentals

A wooden cabin with a garage, surrounded by trees and a gravel driveway.

1. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is NT$9,387
NT$16,629 total
includes taxes & fees
Oct 28 - Oct 29
The Pond Cabin
A bed with a dark quilted cover, two beige pillows, and a headboard with two wall-mounted lamps.

2. Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (23 reviews)
"Very clean and cozy cabins!"
United States
Abraham
The price is NT$4,779
NT$5,400 total
includes taxes & fees
Oct 22 - Oct 23
Canal Cabins
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

3. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (52 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is NT$4,389
NT$4,928 total
includes taxes & fees
Oct 22 - Oct 23
Roadhaven1830
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

4. Schilling House

Schilling House
3.0 star property
Bolivar
The price is NT$8,907
NT$11,156 total
includes taxes & fees
Oct 22 - Oct 23
Schilling House
A cozy living room with a fireplace, a dining area with a table and chairs, and a large window overlooking a forest.

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 NT$4,959
NT$8,832 total
includes taxes & fees
Oct 29 - Oct 30
2-Bedroom cabin Hot tub Fireplace PS5
A modern living room with a fireplace, a large sofa, a coffee table, and a TV mounted on the wall.

6. 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 NT$5,851
NT$10,873 total
includes taxes & fees
Oct 29 - Oct 30
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A garden with a wooden pergola, a table with chairs, and a variety of plants and flowers.

7. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is NT$13,231
NT$22,075 total
includes taxes & fees
Oct 22 - Oct 23
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

8/10 Good
"Nice hotel. I would stay here again."
Kenneth 1-night trip
Posted 3 hours ago
Comfort Inn & Suites 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 15 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 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 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.