Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

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, (31 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.
The price is ￥30,311
￥36,952 total
includes taxes & fees
Apr 16 - Apr 17
Blue Mountain Cabin, secluded, perfect for couples, near main road
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (17 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is ￥21,555
￥34,654 total
includes taxes & fees
Apr 6 - Apr 7
Mountain View Bungalow in Front Royal
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is ￥25,525
￥51,557 total
includes taxes & fees
Apr 5 - Apr 6
Newly renovated Farm cottage with Mountain views
Interior

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (30 reviews)
"The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience."
United States
Jennifer d.
The price is ￥33,052
￥70,975 total
includes taxes & fees
Apr 5 - Apr 6
Mountain cabin near national park & wineries
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.
The price is ￥22,833
￥57,061 total
includes taxes & fees
Apr 20 - Apr 21
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
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.
The price is ￥23,690
￥34,930 total
includes taxes & fees
Apr 12 - Apr 13
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Smart TV

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (16 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is ￥29,513
￥52,779 total
includes taxes & fees
Apr 6 - Apr 7
Nostalgia Lane in the heart of the city
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stayed "
United States
Mike F.
The price is ￥21,537
￥36,073 total
includes taxes & fees
Apr 12 - Apr 13
Apple Mountain Retreat
Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (6 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.
The price is ￥21,555
￥43,139 total
includes taxes & fees
Apr 6 - Apr 7
Lunar Loft, with mountain views
Interior

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is ￥17,548
￥30,727 total
includes taxes & fees
Apr 5 - Apr 6
Rosamond nice downtown studio apt
Property grounds

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
The price is ￥20,952
￥62,208 total
includes taxes & fees
Apr 9 - Apr 10
Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is ￥28,396
￥51,513 total
includes taxes & fees
Apr 5 - Apr 6
Morocco Loft 2BR overlooking city walking mall
Living area

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
Blue Mountain House - Hot Tub, Grill, Fire Table
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.
The price is ￥46,663
￥68,627 total
includes taxes & fees
Apr 6 - Apr 7
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
TV, offices

Shenandoah mountain cottage w/hot tub & fire pit

Shenandoah mountain cottage w/hot tub & fire pit
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.
Shenandoah mountain cottage w/hot tub & fire pit
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.
The price is ￥38,128
￥82,176 total
includes taxes & fees
Apr 15 - Apr 16
The Pond Cabin: Hot Tub & Stocked Pond
Interior

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (27 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
The price is ￥31,906
￥72,407 total
includes taxes & fees
Apr 5 - Apr 6
Hidden Gem on Hidden Valley Lane
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
7.8 out of 10, Good, (7 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.
The price is ￥15,793
￥33,434 total
includes taxes & fees
Apr 6 - Apr 7
The Queen of Winchester Three Bedroom with Upper Level Deck
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, (3 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is ￥23,132
￥28,641 total
includes taxes & fees
Apr 27 - Apr 28
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Living area

SkyCrest Cabin: Panoramic Shenandoah River Views with Sauna, Hot Tub & Game Room

SkyCrest Cabin: Panoramic Shenandoah River Views with Sauna, Hot Tub & Game Room
Front Royal
SkyCrest Cabin: Panoramic Shenandoah River Views with Sauna, Hot Tub & Game Room
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Parking was convenient. I didn’t get up in time for the breakfast. "
Martin 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Winchester

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:

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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?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This vacation home rental near Winchester offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable 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 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 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.