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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Winchester vacation rentals

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.
$215 nightly
The price is $237
Jun 28 - Jun 29
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
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.
$205 nightly
The price is $226
Jun 30 - Jul 1
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Outdoor spa tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
$368 nightly
The price is $406
Jul 27 - Jul 28
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Interior

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (31 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
$383 nightly
The price is $422
Jun 28 - Jun 29
Total with taxes and fees
Mountain cabin near national park & wineries
Cabin, Private Bathroom (The Pond Cabin) | Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Jun 29 - Jun 30
Total with taxes and fees
The Pond Cabin
Exterior

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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
$412 nightly
The price is $454
Jul 12 - Jul 13
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, (29 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.
$200 nightly
The price is $223
Jun 30 - Jul 1
Total with taxes and fees
Mountain View Bungalow in Front Royal
TV, offices

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
$287 nightly
The price is $307
Jun 28 - Jun 29
Total with taxes and fees
Mountain home w/ hot tub & sunroom
Cookware/dishes/utensils

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (34 reviews)
"We always love staying here. We have stayed at The Pond Cabin multiple times and will continue doing so as long as it is available!"
United States
Mary S.
$473 nightly
The price is $522
Jun 29 - Jun 30
Total with taxes and fees
The Pond Cabin: Hot Tub & Stocked Pond
Fridge, microwave, oven, stovetop

Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
$348 nightly
The price is $401
Jun 28 - Jun 29
Total with taxes and fees
Bend of Brothers’ | Riverfront Cottage Shenandoah
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
$299 nightly
The price is $339
Jun 28 - Jun 29
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
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.
$239 nightly
The price is $272
Jul 7 - Jul 8
Total with taxes and fees
Lunar Loft, 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, (6 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
$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
Interior

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

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
$324 nightly
The price is $360
Jun 30 - Jul 1
Total with taxes and fees
Bluemont home just minutes to wineries, breweries, hiking and more!
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.
$423 nightly
The price is $454
Jun 28 - Jun 29
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
Outdoor dining

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (3 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
$245 nightly
The price is $263
Jun 28 - Jun 29
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
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
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.
$388 nightly
The price is $428
Jun 30 - Jul 1
Total with taxes and fees
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Smart TV, books

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
$203 nightly
The price is $230
Jul 7 - Jul 8
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Terrace/patio

All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
$511 nightly
The price is $564
Jul 15 - Jul 16
Total with taxes and fees
All-Inclusive 4BR | Mountain Views | Hot Tub
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Beautiful building located in the heart of the historic district. The rooms were well-appointed, with comfortable bedding/pillows, a fireplace, and a multi-jet shower and jacuzzi tub where we stayed. There was a very good musical act performing in the hotel bar when we checked in Friday night and the atmosphere seemed lively. Would definitely recommend for a weekend getaway!"
Bruce 1-night trip
Posted 5 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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 $101 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 Rocking S Ranch 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.