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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Winchester vacation rentals

Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
$348 nightly
The price is $387
Jul 2 - Jul 3
Total with taxes and fees
Bluemont home just minutes to wineries, breweries, hiking and more!
Property grounds

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (36 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
$216 nightly
The price is $238
Jul 1 - Jul 2
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Exterior

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
$401 nightly
The price is $442
Jul 15 - Jul 16
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (31 reviews)
"We had a great stay! The house is cozy and just perfect for a private get away. The hosts were very communicative and wonderful, we will be back! "
United States
Virginia A.
$198 nightly
The price is $220
Jul 2 - Jul 3
Total with taxes and fees
Mountain View Bungalow in Front Royal
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (14 reviews)
"Excellent place to stay. Shelly is an excellent host. Nice location "
United States
Lisa H.
$390 nightly
The price is $434
Jul 1 - Jul 2
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
$237 nightly
The price is $270
Jul 7 - Jul 8
Total with taxes and fees
Lunar Loft, with mountain views
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
$304 nightly
The price is $338
Jul 2 - Jul 3
Total with taxes and fees
Comfy Getaway in Strasburg, VA!
Interior

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (29 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
$426 nightly
The price is $457
Jul 1 - Jul 2
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveler
$155 nightly
The price is $176
Jul 1 - Jul 2
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
TV

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
$220 nightly
The price is $243
Jul 20 - Jul 21
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Property grounds

The Haven at Turkey Run • Hot Tub, Fire Pit, Games

The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Strasburg
10.0 out of 10, Exceptional, (14 reviews)
"Loved the creek and the hot tub!!! Cant say enough good things about this place"
United States
Maxx H.
$387 nightly
The price is $427
Jul 1 - Jul 2
Total with taxes and fees
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Cabin, Private Bathroom (The Pond Cabin) | Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Jul 12 - Jul 13
Total with taxes and fees
The Pond Cabin
Fridge, microwave, oven, stovetop

Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
$351 nightly
The price is $404
Jul 1 - Jul 2
Total with taxes and fees
Bend of Brothers’ | Riverfront Cottage Shenandoah
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
$197 nightly
The price is $208
Jul 1 - Jul 2
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
Terrace/patio

All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
$505 nightly
The price is $557
Jul 19 - Jul 20
Total with taxes and fees
All-Inclusive 4BR | Mountain Views | Hot Tub
Outdoor spa tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$330 nightly
The price is $363
Jul 12 - Jul 13
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Property grounds

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
10.0 out of 10, Exceptional, (11 reviews)
"Nice owner, great place"
United States
Leslie C.
$251 nightly
The price is $286
Jul 1 - Jul 2
Total with taxes and fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Private kitchen

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Winchester
$226 nightly
The price is $256
Jul 7 - Jul 8
Total with taxes and fees
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
$275 nightly
The price is $303
Jul 15 - Jul 16
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
Terrace/patio

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (7 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
$165 nightly
The price is $184
Jul 12 - Jul 13
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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
"Great hotel! Clean room, good amenities, good breakfast."
Jacqueline 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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Winchester offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Nalls Farm Market are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

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.