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

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Our top choices for Winchester apartments

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 $127
CA $282 total
includes taxes & fees
Aug 25 - Aug 26
The Queen of Winchester Three Bedroom with Upper Level Deck

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.
The price is CA $223
CA $369 total
includes taxes & fees
Jul 31 - Aug 1
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

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.
The price is CA $218
CA $364 total
includes taxes & fees
Jul 26 - Jul 27
Cameron Grace Brand New 1BR 1BA apt downtown Winchester

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 $209
CA $369 total
includes taxes & fees
Jul 26 - Jul 27
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

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 $239
CA $462 total
includes taxes & fees
Jul 31 - Aug 1
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

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 $155
CA $281 total
includes taxes & fees
Aug 16 - Aug 17
The Stock Exchange downtown 3rd floor studio apt

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 $226
CA $428 total
includes taxes & fees
Jul 26 - Jul 27
Morocco Loft 2BR overlooking city walking mall

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 $275
CA $351 total
includes taxes & fees
Jul 27 - Jul 28
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

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 $261
CA $473 total
includes taxes & fees
Aug 2 - Aug 3
Nostalgia Lane in the heart of the city

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 $206
CA $366 total
includes taxes & fees
Jul 26 - Jul 27
Yellow Submarine trendy basement apt and courtyard

Apple Mountain Retreat

Apple Mountain Retreat
Linden
9.8 out of 10, Exceptional, (27 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $190
CA $325 total
includes taxes & fees
Jul 26 - Jul 27
Apple Mountain Retreat

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 $289
CA $527 total
includes taxes & fees
Jul 30 - Jul 31
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

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 $190
CA $382 total
includes taxes & fees
Aug 5 - Aug 6
Lunar Loft, with mountain views

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)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is CA $313
CA $559 total
includes taxes & fees
Jul 26 - Jul 27
Scarborough Fair walk to downtown two story apt

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
9.8 out of 10, Exceptional, (12 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is CA $200
CA $416 total
includes taxes & fees
Aug 10 - Aug 11
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

"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 $306
CA $374 total
includes taxes & fees
Jul 26 - Jul 27
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Winchester
The price is CA $218
CA $364 total
includes taxes & fees
Jul 26 - Jul 27
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Berkeley Springs
10.0 out of 10, Exceptional, (1 review)
"Everything from booking the stay to arriving and checking in was quick and convenient. The host emailed us directions and was easy to navigate toThe owl was just the perfect size for "
United States
kayla c.
The price is CA $118
CA $285 total
includes taxes & fees
Jul 26 - Jul 27
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (65 reviews)
"The apartment was cozy and just as described. Check-in was super easy and the owners were very responsive to any questions we had. Thanks for a super pleasant stay!"
United States
Candi M.
The price is CA $140
CA $254 total
includes taxes & fees
Jul 26 - Jul 27
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
9.6 out of 10, Exceptional, (8 reviews)
"Wonderful stay! Will be back! "
United States
Shanna A.
The price is CA $271
CA $451 total
includes taxes & fees
Jul 29 - Jul 30
Glamping dome w/ hot tub & mountain 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

Find out more about Winchester

Winchester Apartments information

Number of reviews
Accommodation
195 Apartments
Lowest Price
CA $230
Highest Price
CA $230

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 26 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 26 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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