Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

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, (34 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.
$213 nightly
The price is $235
May 24 - May 25
Total with taxes and fees
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, (25 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
$197 nightly
The price is $219
May 26 - May 27
Total with taxes and fees
Mountain View Bungalow in Front Royal
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.
$426 nightly
The price is $457
May 30 - May 31
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
$275 nightly
The price is $303
May 26 - May 27
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
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.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
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.
$471 nightly
The price is $520
May 27 - May 28
Total with taxes and fees
The Pond Cabin: Hot Tub & Stocked Pond
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, (4 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
$165 nightly
The price is $180
Jun 1 - Jun 2
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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.
$307 nightly
The price is $348
May 24 - May 25
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
Interior

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (31 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.
$386 nightly
The price is $426
May 25 - May 26
Total with taxes and fees
Mountain cabin near national park & wineries
4 bedrooms, desk, iron/ironing board, travel crib

Prima Mountain Cabin • Hot Tub • Game Room

Prima Mountain Cabin • Hot Tub • Game Room
Front Royal
10.0 out of 10, Exceptional, (6 reviews)
"Great property. Location is perfect with amazing view. Great house and amenities. "
United States
Michael M.
$463 nightly
The price is $480
Jun 16 - Jun 17
Total with taxes and fees
Prima Mountain Cabin • Hot Tub • Game Room
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.
$329 nightly
The price is $362
May 26 - May 27
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stayed "
United States
Mike F.
$212 nightly
The price is $234
May 25 - May 26
Total with taxes and fees
Apple Mountain Retreat
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.
$299 nightly
The price is $321
Jun 1 - Jun 2
Total with taxes and fees
Mountain home w/ hot tub & sunroom
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
9.2 out of 10, Wonderful, (5 reviews)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
$438 nightly
The price is $483
May 31 - Jun 1
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
TV, fireplace, offices

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
$404 nightly
The price is $446
May 25 - May 26
Total with taxes and fees
Blue Mountain House - Hot Tub, Grill, Fire Table
Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (8 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.
$235 nightly
The price is $268
May 25 - May 26
Total with taxes and fees
Lunar Loft, with mountain views
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
May 24 - May 25
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
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.
$286 nightly
The price is $324
May 24 - May 25
Total with taxes and fees
Nostalgia Lane in the heart of the city
Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (8 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
$213 nightly
The price is $241
May 22 - May 23
Total with taxes and fees
Pretty Little Apt by the Train II
Outdoor dining

Shenandoah Twilight | Cozy Cabin with Hot Tub & Sunset Views

Shenandoah Twilight | Cozy Cabin with Hot Tub & Sunset Views
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.
$364 nightly
The price is $402
Jun 7 - Jun 8
Total with taxes and fees
Shenandoah Twilight | Cozy Cabin with Hot Tub & Sunset Views
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

APM Inn & Suites

APM Inn & Suites

10/10 Excellent
"Good place"
Orlando 1-night trip
Posted 6 hours ago
APM Inn & Suites

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 $133 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?

Private mountaintop cabin with hot tub, pool table, and breathtaking views: This vacation home rental near Winchester is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals will I find in Winchester?

Choose from 13 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 Apple Blossom Mall.

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.