Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester vacation rentals

Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (13 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is ￥20,859
￥34,396 total
includes taxes & fees
Feb 12 - Feb 13
Mountain View Bungalow in Front Royal
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, (28 reviews)
"Clean,Comfy, cozy, secluded and quiet!!! Perfect spot for a little getaway!"
United States
Morgan S.
The price is ￥27,812
￥34,255 total
includes taxes & fees
Feb 19 - Feb 20
Blue Mountain Cabin, secluded, perfect for couples, near main road
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, (1 review)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is ￥20,164
￥25,301 total
includes taxes & fees
Feb 17 - Feb 18
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Outdoor dining

Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (15 reviews)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
The price is ￥25,494
￥66,295 total
includes taxes & fees
Feb 12 - Feb 13
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Terrace/patio

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
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 ￥16,370
￥55,039 total
includes taxes & fees
Feb 18 - Feb 19
"Prima BnB" a Superb 4-bedroom cottage on the mountain near 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, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is ￥24,722
￥50,105 total
includes taxes & fees
Feb 24 - Feb 25
Newly renovated Farm cottage with Mountain views
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 ￥20,859
￥41,746 total
includes taxes & fees
Feb 12 - Feb 13
Lunar Loft, with mountain views
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 ￥30,902
￥70,129 total
includes taxes & fees
Feb 18 - Feb 19
Hidden Gem on Hidden Valley Lane
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is ￥30,918
￥54,492 total
includes taxes & fees
Feb 15 - Feb 16
Cameron Charmer pristine downtown apt with double master suites
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.
The price is ￥19,314
￥56,752 total
includes taxes & fees
Feb 23 - Feb 24
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Indoor spa tub

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
The price is ￥40,945
￥87,428 total
includes taxes & fees
Feb 12 - Feb 13
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
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, (15 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is ￥28,584
￥51,467 total
includes taxes & fees
Feb 12 - Feb 13
Nostalgia Lane in the heart of the city
TV, fireplace, offices

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
The price is ￥32,948
￥75,096 total
includes taxes & fees
Feb 16 - Feb 17
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
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 ￥16,996
￥29,760 total
includes taxes & fees
Feb 12 - Feb 13
Rosamond nice downtown studio apt
Outdoor dining

Shenandoah Twilight | Cozy Cabin w/ hot tub

Shenandoah Twilight | Cozy Cabin w/ hot tub
Front Royal
9.0 out of 10, Wonderful, (2 reviews)
"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "
United States
Wilson (Wally) W.
The price is ￥33,220
￥72,090 total
includes taxes & fees
Feb 16 - Feb 17
Shenandoah Twilight | Cozy Cabin w/ hot tub
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, (11 reviews)
"Loved the creek and the hot tub!!! Cant say enough good things about this place"
United States
Maxx H.
The price is ￥26,267
￥69,193 total
includes taxes & fees
Feb 12 - Feb 13
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
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 ￥25,494
￥37,835 total
includes taxes & fees
Mar 1 - Mar 2
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Property grounds

The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River
Front Royal
10.0 out of 10, Exceptional, (15 reviews)
"We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!"
United States
Dan P.
The price is ￥24,630
￥65,170 total
includes taxes & fees
Feb 23 - Feb 24
The Vue - Mountain Top hot tub overlooking the Shenandoah River
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)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
The price is ￥36,928
￥79,420 total
includes taxes & fees
Feb 24 - Feb 25
The Pond Cabin: Hot Tub & Stocked Pond
TV, offices

Mountain cottage w/hot tub & lake access

Mountain cottage w/hot tub & lake access
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.
The price is ￥26,415
￥48,698 total
includes taxes & fees
Feb 18 - Feb 19
Mountain cottage w/hot tub & lake access
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

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

10/10 Excellent
"Room with Jacuzzi tub in it was so nice. Everything spotless great stay! Recommended! "
Janice 2-night trip
Posted 3 days ago
Hilton Garden Inn Dulles North

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?

Secluded River Cabin Getaway (Masten Cabin): This vacation home rental near Winchester is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.