Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Winchester vacation rentals

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.
$151 nightly
The price is $164
Jan 28 - Jan 29
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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, (12 reviews)
"Our family had a lovely time at The Vue! It was clean, comfortable, and had everything we needed for a quick getaway. The mountain view was truly incredible and we enjoyed watching the sunrise with our coffee on the back deck. While there's not much of a yard, our pup enjoyed the outdoor space too! Thank for being a part of our family's special memories. We'll be back!"
United States
Alyssa L.
$406 nightly
The price is $448
Feb 1 - Feb 2
Total with taxes and fees
The Vue - Mountain Top hot tub overlooking the Shenandoah River
Exterior

The Royal Cabin | Private Getaway w/ Hot Tub

The Royal Cabin | Private Getaway w/ Hot Tub
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"House was very clean and well stocked. Great outdoor games for all ages. Perfect for our family and friends as we celebrated a wedding."
United States
mollie g.
$676 nightly
The price is $746
Jan 28 - Jan 29
Total with taxes and fees
The Royal Cabin | Private Getaway w/ Hot Tub
Microwave, oven, stovetop, dishwasher

Shenandoah River Retreat: Pool Table and Fireplace

Shenandoah River Retreat: Pool Table and Fireplace
Front Royal
$307 nightly
The price is $339
Feb 9 - Feb 10
Total with taxes and fees
Shenandoah River Retreat: Pool Table and Fireplace
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, (2 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$257 nightly
The price is $283
Jan 27 - Jan 28
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
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.
$496 nightly
The price is $547
Feb 2 - Feb 3
Total with taxes and fees
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Smart TV, fireplace

Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
$346 nightly
The price is $392
Jan 27 - Jan 28
Total with taxes and fees
Scarborough Fair walk to downtown two story apt
TV, fireplace, offices

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
9.8 out of 10, Exceptional, (10 reviews)
"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.
$519 nightly
The price is $572
Feb 1 - Feb 2
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
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.
$296 nightly
The price is $326
Jan 28 - Jan 29
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
Smart TV, books

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.6 out of 10, Excellent, (4 reviews)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
$203 nightly
The price is $230
Jan 27 - Jan 28
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV

Welcome to the Ladybug Retreat!

Welcome to the Ladybug Retreat!
Boyce
10.0 out of 10, Exceptional, (1 review)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
United States
Catherine A.
$367 nightly
The price is $405
Jan 27 - Jan 28
Total with taxes and fees
Welcome to the Ladybug Retreat!
Dining

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA
Linden
10.0 out of 10, Exceptional, (3 reviews)
"Megan was exceptional at communications, the property was perfect for our Family Thanksgiving. "
United States
Lynne S.
$447 nightly
The price is $493
Jan 27 - Jan 28
Total with taxes and fees
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA
Dining

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (6 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
$313 nightly
The price is $355
Jan 27 - Jan 28
Total with taxes and fees
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
$184 nightly
The price is $200
Feb 22 - Feb 23
Total with taxes and fees
Very charming & spacious 2 bedrm
Outdoor dining

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Front Royal
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
$603 nightly
The price is $665
Jan 28 - Jan 29
Total with taxes and fees
Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
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.
$308 nightly
The price is $349
Feb 15 - Feb 16
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
Smart TV, fireplace

On the river ~ hot tub ~ serene river views ~ fire pit

On the river ~ hot tub ~ serene river views ~ fire pit
Strasburg
10.0 out of 10, Exceptional, (29 reviews)
"Our stay was wonderful. Everything was clean and inviting. The views were great!"
United States
Ryann S.
$503 nightly
The price is $555
Feb 1 - Feb 2
Total with taxes and fees
On the river ~ hot tub ~ serene river views ~ fire pit
Interior

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful space; helpful host."
United States
Sally C.
$344 nightly
The price is $390
Feb 2 - Feb 3
Total with taxes and fees
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
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, (27 reviews)
"Great place to relax"
United States
Judy
$200 nightly
The price is $221
Feb 2 - Feb 3
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
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.
$333 nightly
The price is $367
Feb 4 - Feb 5
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"It was a great experience "
Emelyne 4-night trip
Posted 1 day ago
Hampton Inn Martinsburg

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 $208 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?

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace: This vacation home rental near Winchester offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Winchester?

Choose from 15 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 Jim Barnett Park 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.