Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

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)
"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.
$213 nightly
The price is $235
Apr 1 - Apr 2
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, (17 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
$197 nightly
The price is $219
Apr 2 - Apr 3
Total with taxes and fees
Mountain View Bungalow in Front Royal
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.
$293 nightly
The price is $332
Mar 31 - Apr 1
Total with taxes and fees
Nostalgia Lane in the heart of the city
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.
$295 nightly
The price is $325
Apr 2 - Apr 3
Total with taxes and fees
Newly renovated Farm cottage 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.
$423 nightly
The price is $454
Mar 31 - Apr 1
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
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.
$373 nightly
The price is $411
Apr 14 - Apr 15
Total with taxes and fees
Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
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.
$201 nightly
The price is $221
Mar 31 - Apr 1
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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)
"Quaint, comfortable, clean, and very quiet setting in the woods. The host's emails were both informative and expressed a strong desire to be sure everything was good."
United States
Ann L.
$295 nightly
The price is $316
Apr 2 - Apr 3
Total with taxes and fees
Shenandoah mountain cottage w/hot tub & fire pit
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.
$404 nightly
The price is $446
Mar 31 - Apr 1
Total with taxes and fees
Mountain cabin near national park & wineries
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, (2 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
$165 nightly
The price is $180
Apr 8 - Apr 9
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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.
$320 nightly
The price is $353
Apr 20 - Apr 21
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (6 reviews)
"Property was as described, location for us being horse people was perfect. A bottle of wine & yummy assorted dessert box a nice treat from owner! Will return for sure."
United States
Lori L.
$236 nightly
The price is $269
Mar 31 - Apr 1
Total with taxes and fees
Lunar Loft, with mountain views
Property grounds

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
10.0 out of 10, Exceptional, (7 reviews)
"The place was situated perfectly within distance to Bluemont Vineyard. The host, Jessica is great. Great communication and the area is spacious and cozy. We will definitely be staying here again when in the area. The dogs, Cooper and Zeus, who live upstairs are just wonderful and friendly. 10/10 recommend. "
United States
Karen P.
$237 nightly
The price is $270
Mar 31 - Apr 1
Total with taxes and fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
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.
$205 nightly
The price is $226
Mar 31 - Apr 1
Total with taxes and fees
Apple Mountain Retreat
Outdoor spa tub

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (32 reviews)
"A very spacious and well equipped home to get away from it all; but, also convenient to Winchester for a night out. The fenced in areas for dogs were lovely."
United States
David A.
$554 nightly
The price is $611
Apr 2 - Apr 3
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Terrace/patio

The Apple Mountain House

The Apple Mountain House
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
$442 nightly
The price is $488
Apr 5 - Apr 6
Total with taxes and fees
The Apple Mountain House
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.
$327 nightly
The price is $361
Apr 19 - Apr 20
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (7 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.
$190 nightly
The price is $215
Apr 12 - Apr 13
Total with taxes and fees
Pretty Little Apt by the Train II
Interior

Litorum - a place to land, breathe, and reset.

Litorum - a place to land, breathe, and reset.
Front Royal
$335 nightly
The price is $370
Mar 31 - Apr 1
Total with taxes and fees
Litorum - a place to land, breathe, and reset.
Exterior

Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
$256 nightly
The price is $282
Mar 31 - Apr 1
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
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

10/10 Excellent
"Being greeted by an alert and cheerful front desk person when checking in at 1 am set the tone for feeling comfortable about how the rest of the stay was going to go. i'll definitely try other Microtel Inn & Suites by Wyndham on my next trip. "
Mark 2-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Winchester

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 $309 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?

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 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.