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Apartments in Winchester for Rent

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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 ￥14,596
￥32,965 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 traveler
The price is ￥16,218
￥28,482 total
includes taxes & fees
Jul 20 - Jul 21
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 ￥17,840
￥32,157 total
includes taxes & fees
Jul 12 - Jul 13
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 ￥30,563
￥57,283 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 ￥21,894
￥37,924 total
includes taxes & fees
Jul 10 - Jul 11
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 ￥23,678
￥41,159 total
includes taxes & fees
Aug 3 - Aug 4
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 ￥24,327
￥47,332 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 ￥30,003
￥53,470 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 ￥22,381
￥38,036 total
includes taxes & fees
Jul 20 - Jul 21
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 ￥33,327
￥57,652 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 ￥36,004
￥64,129 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 ￥28,868
￥52,553 total
includes taxes & fees
Jul 20 - Jul 21
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 ￥24,003
￥42,446 total
includes taxes & fees
Jul 15 - Jul 16
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 ￥31,625
￥39,690 total
includes taxes & fees
Aug 2 - Aug 3
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 ￥35,193
￥43,156 total
includes taxes & fees
Jul 19 - Jul 20
"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.
The price is ￥25,138
￥42,079 total
includes taxes & fees
Jul 10 - Jul 11
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 ￥16,768
￥18,830 total
includes taxes & fees
Aug 9 - Aug 10
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 ￥14,384
￥27,242 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 ￥16,640
￥30,592 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

Skyland

Skyland

8/10 Good
"When I initially checked in the person at the desk said they upgraded me to a room with AC (it had been very hot) because the traditional rooms on Expedia apparently don’t have AC? I wouldn’t have guessed that when booking. The room I received was rustic as most of Skyland mentions ahead of time but after one night in, I noticed the coffee maker didn’t work, and the hot water in the shower wasn’t that great. As I was showing I saw what looked like a cockroach (it could also have been some sort of large beetle) but it didn’t set well with me so I called the front desk and they immediately moved me to a premium room, which was much better and the shower and patio were great. They WERE amazingly accommodating! So off to a rocky start but otherwise the food was delicious and the views were spectacular!"
Heidi 3-night trip
Posted 3 hours ago
Skyland

Find out more about Winchester

Winchester Apartments information

Number of reviews
243
Accommodation
203 Apartments
Lowest Price
￥18,830
Highest Price
￥64,129

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.