Winchester Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Winchester holiday rentals

Property grounds

Cabin in Front Royal

Blue Mountain Cabin, secluded, perfect for couples, near main road
10.0 out of 10, Exceptional, (31 reviews)
"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."
United States
Tom C.
The price is HK$1,488
HK$1,840 total
includes taxes & fees
24 Mar - 25 Mar
Blue Mountain Cabin, secluded, perfect for couples, near main road
Terrace/patio

Cabin in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
10.0 out of 10, Exceptional, (2 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is HK$1,022
HK$1,283 total
includes taxes & fees
23 Mar - 24 Mar
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Property grounds

Holiday Home in Strasburg

Newly renovated Farm cottage with Mountain views
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 HK$1,253
HK$2,549 total
includes taxes & fees
23 Mar - 24 Mar
Newly renovated Farm cottage with Mountain views
Property grounds

Cabin in Front Royal

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
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 HK$1,287
HK$3,389 total
includes taxes & fees
22 Mar - 23 Mar
Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
Terrace/patio

Holiday Home in Front Royal

Mountain View Bungalow in Front Royal
10.0 out of 10, Exceptional, (17 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 HK$1,057
HK$1,726 total
includes taxes & fees
22 Mar - 23 Mar
Mountain View Bungalow in Front Royal
Outdoor spa tub

Cabin in Linden

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
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 HK$1,104
HK$2,713 total
includes taxes & fees
15 Apr - 16 Apr
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Smart TV, offices

Holiday Home in Middletown

Dog-Friendly Cottage w Playground, Grill & Games
9.6 out of 10, Exceptional, (17 reviews)
"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "
United States
Corrin D.
The price is HK$1,260
HK$2,568 total
includes taxes & fees
22 Mar - 23 Mar
Dog-Friendly Cottage w Playground, Grill & Games
Property grounds

Apartment in Bluemont

Lunar Loft, with mountain views
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 HK$1,057
HK$2,072 total
includes taxes & fees
31 Mar - 1 Apr
Lunar Loft, with mountain views
Interior

Cabin in Linden

Hidden Gem on Hidden Valley Lane
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 HK$1,567
HK$3,572 total
includes taxes & fees
22 Mar - 23 Mar
Hidden Gem on Hidden Valley Lane
Smart TV

Apartment in Old Town Winchester

Nostalgia Lane in the heart of the city
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 HK$1,449
HK$2,556 total
includes taxes & fees
1 Apr - 2 Apr
Nostalgia Lane in the heart of the city
TV

Cottage in Front Royal

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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 HK$1,163
HK$1,715 total
includes taxes & fees
30 Mar - 31 Mar
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Outdoor dining

Cabin in Front Royal

Shenandoah Twilight | Cozy Cabin w/ hot tub
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 HK$1,645
HK$3,620 total
includes taxes & fees
23 Mar - 24 Mar
Shenandoah Twilight | Cozy Cabin w/ hot tub
Cookware/dishes/utensils

Cabin in Linden

The Pond Cabin: Hot Tub & Stocked Pond
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 HK$1,872
HK$4,052 total
includes taxes & fees
23 Mar - 24 Mar
The Pond Cabin: Hot Tub & Stocked Pond
TV, offices

Holiday Home in Front Royal

Shenandoah mountain cottage w/ hot tub & lake
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 HK$1,339
HK$2,478 total
includes taxes & fees
22 Mar - 23 Mar
Shenandoah mountain cottage w/ hot tub & lake
Living area

Apartment in Old Town Winchester

Morocco Loft 2BR overlooking city walking mall
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is HK$1,394
HK$2,441 total
includes taxes & fees
19 Apr - 20 Apr
Morocco Loft 2BR overlooking city walking mall
Property grounds

Apartment in Bluemont

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
10.0 out of 10, Exceptional, (7 reviews)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is HK$1,050
HK$2,081 total
includes taxes & fees
25 Mar - 26 Mar
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Interior

Holiday Home in Winchester Historic District

Indigo Blue modern open vibe on tree lined street
10.0 out of 10, Exceptional, (13 reviews)
"Perfect for our needs for our daughter’s graduation!"
United States
Chris and Michelle P.
The price is HK$1,723
HK$3,151 total
includes taxes & fees
1 Apr - 2 Apr
Indigo Blue modern open vibe on tree lined street
Outdoor dining

Cabin in Linden

Skyland Hideaway | Mountain Cabin w/ Hot Tub
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 HK$1,292
HK$3,378 total
includes taxes & fees
2 Apr - 3 Apr
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Terrace/patio

Holiday Home in Front Royal

The Apple Mountain House
9.8 out of 10, Exceptional, (11 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The Apple Mountain House
Property grounds

Apartment in Linden

Apple Mountain Retreat
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stayed "
United States
Mike F.
The price is HK$1,057
HK$1,789 total
includes taxes & fees
22 Mar - 23 Mar
Apple Mountain Retreat
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

8/10 Good
"Excellent staff who changed our room so we weren’t next to the Interstate. It was still a bit noisy when loud trucks went by. Otherwise our room was very nice."
Susan 1-night trip
Posted 5 hours ago
Microtel 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:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

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

How many holiday rentals will I find in Winchester?

Choose from 13 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of the 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 Apple Blossom Mall.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.