Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Winchester vacation rentals

Garden
Roadhaven1830

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (38)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
The price is P7,946
P8,924 total
includes taxes & fees
Feb 1 - Feb 2
Roadhaven1830
Exterior
2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
9.4 out of 10, Exceptional, (3)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is P9,387
P16,426 total
includes taxes & fees
Jan 4 - Jan 5
2-Bedroom cabin Hot tub Fireplace PS5
Interior
Balcony & Pool Access: Modern Gainesville Home

Balcony & Pool Access: Modern Gainesville Home

Balcony & Pool Access: Modern Gainesville Home
3.5 star property
Gainesville
Balcony & Pool Access: Modern Gainesville Home
1 bedroom, laptop workspace, free WiFi
Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin

Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin

Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin
2.5 star property
Mount Jackson
The price is P10,054
P17,941 total
includes taxes & fees
Feb 3 - Feb 4
Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin
Interior
'thomson Farm' Classic Home < 10 Mi to Vineyards!

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

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is P63,939
P107,581 total
includes taxes & fees
Jan 4 - Jan 5
'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

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent
"The room was clean, and the breakfast was plentiful. The staff was very friendly and helpful. This was the quietest stay I've had on my trips to Wincheater."
Jay 2-night trip
Posted 4 days ago
Hampton Inn Winchester N/Conference Center, VA

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
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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 Nalls Farm Market 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.