A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winchester apartments

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.
The price is CA $126
CA $288 total
includes taxes & fees
Jul 13 - Jul 14
The Queen of Winchester Three Bedroom with Upper Level Deck
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 traveller
The price is CA $142
CA $249 total
includes taxes & fees
Jul 26 - Jul 27
Cozy English Basement Apt quiet but close to downtown
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is CA $156
CA $284 total
includes taxes & fees
Jul 13 - Jul 14
The Stock Exchange downtown 3rd floor studio apt
Private kitchen

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Winchester
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
The price is CA $266
CA $496 total
includes taxes & fees
Jul 31 - Aug 1
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
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.
The price is CA $191
CA $328 total
includes taxes & fees
Jul 18 - Jul 19
Apple Mountain Retreat
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.
The price is CA $207
CA $368 total
includes taxes & fees
Jul 26 - Jul 27
Yellow Submarine trendy basement apt and courtyard
Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 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.
The price is CA $213
CA $412 total
includes taxes & fees
Aug 4 - Aug 5
Lunar Loft, with mountain views
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.
The price is CA $262
CA $477 total
includes taxes & fees
Jul 13 - Jul 14
Nostalgia Lane in the heart of the city
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)
"Large historic house at a great location "
United States
Bryan T.
The price is CA $196
CA $332 total
includes taxes & fees
Jul 27 - Jul 28
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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.
The price is CA $290
CA $530 total
includes taxes & fees
Jul 12 - Jul 13
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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.
The price is CA $315
CA $563 total
includes taxes & fees
Jul 13 - Jul 14
Scarborough Fair walk to downtown two story apt
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.
The price is CA $227
CA $431 total
includes taxes & fees
Jul 12 - Jul 13
Morocco Loft 2BR overlooking city 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)
The price is CA $210
CA $371 total
includes taxes & fees
Jul 27 - Jul 28
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
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.
The price is CA $276
CA $355 total
includes taxes & fees
Jul 31 - Aug 1
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Outdoor dining

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (3 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is CA $307
CA $377 total
includes taxes & fees
Jul 18 - Jul 19
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Fridge, microwave, oven, stovetop

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Very enjoyable stay right in historical Winchester. We enjoyed walking to a German restaurant for dinner and rested well. "
United States
Brad E.
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (43 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back "
United States
Varnell
The price is CA $148
CA $167 total
includes taxes & fees
Jul 24 - Jul 25
Roadhaven1830
Property grounds

Quiet suite w/ outdoor furniture

Quiet suite w/ outdoor furniture
Luray
9.8 out of 10, Exceptional, (7 reviews)
"The Legacy Inn in Luray was great! Easy to find, easy entry (with a code), within walking distance of dining and outdoor music, and an easy drive to Luray Caverns and Shenandoah National Park. Highly recommend."
United States
Robert
The price is CA $136
CA $250 total
includes taxes & fees
Jul 23 - Jul 24
Quiet suite w/ outdoor furniture
Iron/ironing board, free WiFi, bed sheets

Lovely, clean and walkable in the town of Luray.

Lovely, clean and walkable in the town of Luray.
Luray
9.8 out of 10, Exceptional, (87 reviews)
"Clean room and very walkable to town!"
United States
Corine F.
The price is CA $145
CA $267 total
includes taxes & fees
Jul 13 - Jul 14
Lovely, clean and walkable in the town of Luray.
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Surprised by the affordable Hilton hotel. Room was nice & quiet. We will look for this brand in our future travels."
Marian 1-night trip
Posted 1 hour ago
TRU By Hilton Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
243
Accommodation
195 Apartments
Lowest Price
CA $167
Highest Price
CA $563

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 25 apartments in Winchester for your vacation. Take time to enjoy the array of shops and top-notch restaurants in this vibrant area.
Why choose an apartment versus a traditional hotel?
An apartment is often more spacious than a traditional hotel room and includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for couples who want to stay in a quieter area.
What's the top apartment for a stay in Winchester?
Here is a favorite apartment in the area: Roadhaven1830: Located in Mount Jackson, 39.9 mi/64.2 km from the heart of Winchester. Includes free WiFi, private yards, and Smart TVs. Free parking and a terrace are on site.
How many apartments can I expect to find in Winchester?
Expedia has 25 apartments to book in Winchester.
What will the weather be like in Winchester?
Though weather is just one factor, it can really affect your travel plans, especially when you are planning a longer stay in Winchester. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What should I see in Winchester?
Travelers come to Winchester for its restaurants and shops. Cultural attractions include Winchester Little Theater and Museum of the Shenandoah Valley, whereas Jim Barnett Park and Star Fort Civil War Battlefield are a couple of picturesque spots to enjoy the outdoors. Shenandoah Valley Discovery Museum and Patsy Cline Historic House are other places to visit while you're in town.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) away from the heart of the city. Otherwise, look for flights into Washington Dulles Intl. Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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