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

Apartments in Winchester for Rent

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester apartments

TV

1. 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, (2 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is ￥23,218
￥41,058 total
includes taxes & fees
Sep 21 - Sep 22
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Interior

2. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is ￥17,257
￥30,394 total
includes taxes & fees
Sep 21 - Sep 22
Rosamond nice downtown studio apt
Smart TV, books

3. 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
8.4 out of 10, Very good, (6 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 ￥21,649
￥36,438 total
includes taxes & fees
Sep 21 - Sep 22
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Exterior detail

4. 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 ￥17,257
￥31,106 total
includes taxes & fees
Oct 4 - Oct 5
The Stock Exchange downtown 3rd floor studio apt
Exterior detail

5. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is ￥18,041
￥30,216 total
includes taxes & fees
Sep 30 - Oct 1
The Blue Door steps from Handley Library
Living area

6. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is ￥25,132
￥47,494 total
includes taxes & fees
Sep 22 - Sep 23
Morocco Loft 2BR overlooking city walking mall
Smart TV

7. 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, (18 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 ￥29,023
￥51,369 total
includes taxes & fees
Sep 21 - Sep 22
Nostalgia Lane in the heart of the city
Private kitchen

8. 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, (12 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is ￥30,592
￥39,638 total
includes taxes & fees
Sep 21 - Sep 22
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Dining

9. 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 ￥32,160
￥58,655 total
includes taxes & fees
Sep 22 - Sep 23
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Smart TV, fireplace

10. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (8 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is ￥34,827
￥62,033 total
includes taxes & fees
Sep 21 - Sep 22
Scarborough Fair walk to downtown two story apt
Property grounds

11. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.2 out of 10, Wonderful, (11 reviews)
"Beautiful, peaceful property. We originally lived in the area and were coming back to close out our business in town. The amenities in the home were great and everything was super clean. You definitely get the Northern Virginia rural experience here. Great location and hosts were amazing! Would stay here again!"
United States
Christina C.
The price is ￥21,179
￥42,386 total
includes taxes & fees
Sep 29 - Sep 30
Lunar Loft, with mountain views
Room

12. Downtown Apt 2 • 2BR • Near Park & River • Private

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is ￥25,477
￥42,395 total
includes taxes & fees
Sep 21 - Sep 22
Downtown Apt 2 • 2BR • Near Park & River • Private
Interior

13. Downtown Apt.1 • 2BR/2BA• Near Park/River• Private

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is ￥26,356
￥48,533 total
includes taxes & fees
Sep 21 - Sep 22
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Interior

14. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Outdoor dining

15. "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, (4 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 ￥34,043
￥41,578 total
includes taxes & fees
Sep 27 - Sep 28
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
WiFi

16. Downtown Apt 3 • 2BR • Near Park & River • Private

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
The price is ￥25,477
￥42,047 total
includes taxes & fees
Sep 21 - Sep 22
Downtown Apt 3 • 2BR • Near Park & River • Private
Beach

17. 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, (3 reviews)
"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 ￥10,533
￥28,791 total
includes taxes & fees
Sep 21 - Sep 22
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Interior

18. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (47 reviews)
"Rental was exactly as advertised and in a great location within walking distance of a lot of great spots to check out."
United States
Sarah D.
The price is ￥22,748
￥39,842 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Interior

19. Newly renovated - Walk to Harpers Ferry NP

Newly renovated - Walk to Harpers Ferry NP
Bolivar
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, host was generous and communicative. Location was very close to good hiking spots "
United States
Emma B.
The price is ￥18,041
￥35,823 total
includes taxes & fees
Sep 21 - Sep 22
Newly renovated - Walk to Harpers Ferry NP
Exterior

20. 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, (69 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is ￥15,531
￥28,103 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Getaway near Harper`s Ferry, C&O & Potomac
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"The property was very clean the rooms very nice and the breakfast was nice and hot and included, unlimited bacon, which a lot of hotels I find don’t do that. The lady that took care of the breakfast was on point. They had bagels bread to make toast. They had a pancake machine that spit pancakes out like this was unbelievable delicious."
Belinda 1-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
204
Accommodation
186 Apartments
Lowest Price
￥28,103
Highest Price
￥62,033

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 24 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's a top apartment in the area: Roadhaven1830: Located in Mount Jackson, 39.9 mi/64.2 km away. 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 24 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 Bright Box 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.