Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Winchester vacation rentals

Cabin, Private Bathroom (The Pond Cabin) | Bathroom

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Jun 9 - Jun 10
Total with taxes and fees
The Pond Cabin
Cabin, 1 Queen Bed, Mountain View | Pillowtop beds, free WiFi, bed sheets

Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.6 out of 10, Exceptional, (14 reviews)
"Was an amazing stay. Plan on booking again in future with the kids! "
United States
Brianna
$136 nightly
The price is $154
Jun 13 - Jun 14
Total with taxes and fees
Canal Cabins
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (40 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
$108 nightly
The price is $121
Jun 7 - Jun 8
Total with taxes and fees
Roadhaven1830
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.4 out of 10, Very Good, (7 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
$265 nightly
The price is $274
Jun 9 - Jun 10
Total with taxes and fees
2-Bedroom cabin Hot tub Fireplace PS5
Apartment (1 Bedroom) | Interior

Near Loudoun Wine Trail: Apt w/ Restaurant On-site

Near Loudoun Wine Trail: Apt w/ Restaurant On-site
3.0 star property
Hamilton
$309 nightly
The price is $352
Jun 7 - Jun 8
Total with taxes and fees
Near Loudoun Wine Trail: Apt w/ Restaurant On-site
House (3 Bedrooms) | Interior

Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
Walk to Stores: Home in Historic Shepherdstown!
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"The hotel was very clean and modern with a very minimalist vibe. I like that. No need for unnecessary extras. It was a great venue and we will be sure to stay again. Staff was very pleasant"
James 1-night trip
Posted 6 hours ago
TRU By Hilton Winchester

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Private mountaintop cabin with hot tub, pool table, and breathtaking views: This vacation home rental near Winchester is located on a river and has a balcony, 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 can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals will I find in Winchester?

Choose from 12 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 Jim Barnett Park.

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.