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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Winchester vacation rentals

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
Jul 20 - Jul 21
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
$205 nightly
The price is $216
Jul 29 - Jul 30
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
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
8.8 out of 10, Excellent, (5 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
$207 nightly
The price is $235
Jul 20 - Jul 21
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
TV

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (1 review)
$232 nightly
The price is $263
Jul 26 - Jul 27
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Private kitchen

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Winchester
$227 nightly
The price is $257
Jul 19 - Jul 20
Total with taxes and fees
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Private kitchen

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
$287 nightly
The price is $325
Jul 31 - Aug 1
Total with taxes and fees
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
$267 nightly
The price is $303
Jul 19 - Jul 20
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall
Private kitchen

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful space; helpful host."
United States
Sally C.
$223 nightly
The price is $253
Jul 21 - Jul 22
Total with taxes and fees
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
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
9.8 out of 10, Exceptional, (10 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 $184
Jul 22 - Jul 23
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Smart TV

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (17 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
$283 nightly
The price is $321
Jul 19 - Jul 20
Total with taxes and fees
Nostalgia Lane in the heart of the city
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
$199 nightly
The price is $221
Jul 21 - Jul 22
Total with taxes and fees
Mountain View Bungalow in Front Royal
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, (10 reviews)
"Great location…"
United States
John P.
$332 nightly
The price is $376
Jul 20 - Jul 21
Total with taxes and fees
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
$308 nightly
The price is $349
Aug 2 - Aug 3
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
Smart TV

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
$230 nightly
The price is $261
Jul 26 - Jul 27
Total with taxes and fees
Yellow Submarine trendy basement apt and courtyard
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, (7 reviews)
"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "
United States
Larry E.
$349 nightly
The price is $395
Jul 19 - Jul 20
Total with taxes and fees
Scarborough Fair walk to downtown two story apt
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (47 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
$277 nightly
The price is $306
Jul 20 - Jul 21
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
10.0 out of 10, Exceptional, (1 review)
"Amazingly comfortable place to call home for a few days with plenty of room for activities if you have to stay in! Bedrooms were lovely as were the bathrooms. Updated and very clean!!!! Host was extremely responsive and very easy to work with!! Bonus to bring our pup with us for the stay."
United States
K O.
$319 nightly
The price is $349
Jul 19 - Jul 20
Total with taxes and fees
Bluemont home just minutes to wineries, breweries, hiking and more!
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, (37 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.
$215 nightly
The price is $237
Jul 19 - Jul 20
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stayed "
United States
Mike F.
$212 nightly
The price is $234
Jul 20 - Jul 21
Total with taxes and fees
Apple Mountain Retreat
Exterior

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
$402 nightly
The price is $443
Jul 20 - Jul 21
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"The bed was very comfortable. The bathroom was very roomy and the shower was big! A very nice stay. We would stay there again"
Margaret 1-night trip
Posted less than an hour ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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 $159 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?

Historical home, walkable to many restaurants and shops. : This vacation home near Winchester is located in the city center and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 14 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 Winchester Little 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.