Winchester Vacation Rentals

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Check prices for these dates

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winchester vacation rentals

Garden
Roadhaven1830

Apartment in Mount Jackson

Roadhaven1830
3.0 star property
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 ￥21,111
￥23,707 total
includes taxes & fees
Jan 3 - Jan 4
Roadhaven1830
Exterior
2-Bedroom cabin Hot tub Fireplace PS5

Cabin in The Woods

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
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 ￥24,932
￥43,630 total
includes taxes & fees
Jan 6 - Jan 7
2-Bedroom cabin Hot tub Fireplace PS5
Apartment (4 Bedrooms) | Interior
Balcony & Pool Access: Modern Gainesville Home

Apartment in Gainesville

Balcony & Pool Access: Modern Gainesville Home
3.5 star property
The price is ￥24,708
￥77,783 total
includes taxes & fees
Jan 2 - Jan 3
Balcony & Pool Access: Modern Gainesville Home
Cabin, 1 Bedroom | 1 bedroom, laptop workspace, free WiFi
Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin

Cabin in Mount Jackson

Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin
2.5 star property
The price is ￥26,710
￥47,664 total
includes taxes & fees
Jan 3 - Jan 4
Cozy Tiny Home Retreat On Shenandoah Valley Farm 1 Bedroom Cabin
House (Multiple Bedrooms) | Interior
'thomson Farm' Classic Home < 10 Mi to Vineyards!

Cottage in Leesburg

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
The price is ￥169,829
￥285,746 total
includes taxes & fees
Jan 3 - Jan 4
'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 Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Amazing! General Manager Matt and Front Desk Manager Tracy have put together an absolutely amazing team of employees that ensure every part of your stay @ Hampton by Hilton is comfortable. Warm smiles, safe and comfortable atmosphere, clean rooms, wonderful breakfast all make for a stay worth going back each and every time your in Martinsburg Wv!! "
Andrea 1-night trip
Posted 1 day ago
Hampton Inn Martinsburg

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
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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.

What are some of the best vacation home rentals in Winchester?

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4: This vacation home rental near Winchester is located in the mountains and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.