Winchester Vacation Rentals

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Dec 3 - Dec 4
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Winchester

Interior
Rosamond nice downtown studio apt

Rosamond nice downtown studio apt

Winchester Historic District
8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
United States
John M.
$170 nightly
The price is $193
Dec 4 - Dec 5
Total with taxes and fees
Rosamond nice downtown studio apt
Dining
1800s Cozy Kitchen House in Berryville

1800s Cozy Kitchen House in Berryville

2.0 star property
Berryville
$165 nightly
The price is $185
Dec 4 - Dec 5
Total with taxes and fees
1800s Cozy Kitchen House in Berryville
Exterior
The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch

The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch

Linden
10.0 out of 10, Exceptional, (22)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$305 nightly
The price is $337
Dec 4 - Dec 5
Total with taxes and fees
The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch
Terrace/patio
Cute cabin retreat near Shenandoah National Park and pet friendly!

Cute cabin retreat near Shenandoah National Park and pet friendly!

Linden
9.4 out of 10, Exceptional, (12)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
Cute cabin retreat near Shenandoah National Park and pet friendly!
Smart TV, foosball
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

Stephens City
9.2 out of 10, Wonderful, (7)
"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "
United States
Maureen W.
$291 nightly
The price is $317
Dec 8 - Dec 9
Total with taxes and fees
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
TV, fireplace, offices
Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table

Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table

Linden
10.0 out of 10, Exceptional, (15)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
$331 nightly
The price is $365
Dec 4 - Dec 5
Total with taxes and fees
Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table
Interior
Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm

Winchester
$131 nightly
The price is $143
Dec 14 - Dec 15
Total with taxes and fees
Very charming & spacious 2 bedrm
Property grounds
The Vue - Mountain top hot tub overlooking the Shenandoah River

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
Front Royal
9.8 out of 10, Exceptional, (10)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
$336 nightly
The price is $370
Dec 17 - Dec 18
Total with taxes and fees
The Vue - Mountain top hot tub overlooking the Shenandoah River
Exterior
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

Front Royal
10.0 out of 10, Exceptional, (5)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
$342 nightly
The price is $377
Dec 7 - Dec 8
Total with taxes and fees
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill
Outdoor spa tub
The Honeymoon Cabin | Private Retreat w/ hot tub

The Honeymoon Cabin | Private Retreat w/ hot tub

Front Royal
10.0 out of 10, Exceptional, (2)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
$319 nightly
The price is $352
Dec 4 - Dec 5
Total with taxes and fees
The Honeymoon Cabin | Private Retreat w/ hot tub
Property grounds
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

2.0 star property
Stephens City
$151 nightly
The price is $164
Dec 4 - Dec 5
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Property grounds
"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, (2)
"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.
$357 nightly
The price is $394
Dec 16 - Dec 17
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Smart TV, fireplace, stereo
Escape to Shenandoah River, Hot Tub after a Hike!

Escape to Shenandoah River, Hot Tub after a Hike!

Front Royal
10.0 out of 10, Exceptional, (54)
"Its a nice property to stay. Will be back soon "
United States
Faizan A.
$287 nightly
The price is $317
Dec 8 - Dec 9
Total with taxes and fees
Escape to Shenandoah River, Hot Tub after a Hike!
Living area
Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall

2.0 star property
Old Town Winchester
10.0 out of 10, Exceptional, (2)
"Great property with all the comforts of home"
United States
Kristen R.
$286 nightly
The price is $324
Dec 4 - Dec 5
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall
Exterior detail
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Fauquier County
8.0 out of 10, Very Good, (1)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
$282 nightly
The price is $284
Dec 8 - Dec 9
Total with taxes and fees
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fridge, microwave, oven, stovetop
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal
10.0 out of 10, Exceptional, (11)
"Excelente propiedad "
Mexico
Miguel
$200 nightly
The price is $223
Dec 10 - Dec 11
Total with taxes and fees
Mountain View Bungalow in Front Royal
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)
"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "
United States
Wilson (Wally) W.
$302 nightly
The price is $333
Dec 7 - Dec 8
Total with taxes and fees
Shenandoah Twilight | Cozy Cabin w/ hot tub
Exterior
Farm Suite at Valley View Farm

Farm Suite at Valley View Farm

2.0 star property
Delaplane
$283 nightly
The price is $285
Dec 4 - Dec 5
Total with taxes and fees
Farm Suite at Valley View Farm
Terrace/patio
Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More

Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More

Linden
9.8 out of 10, Exceptional, (10)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
$361 nightly
The price is $398
Dec 9 - Dec 10
Total with taxes and fees
Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More
Property grounds
Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!

Bluemont
8.8 out of 10, Excellent, (6)
"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
Dec 4 - Dec 5
Total with taxes and fees
Private apartment on a beautiful private farm!
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
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
Jeanette 1-night trip
Posted 2 days 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 $224 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?

✨Luxurious Mountaintop Lodge🏔️WOW Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟: This vacation home rental near Winchester is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals will I find in Winchester?

Choose from 17 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 Museum of the Shenandoah Valley. Other places in town to visit include Apple Blossom Mall and Rock Harbor Golf Course.

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.