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

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 HK$1,161
HK$2,036 total
includes taxes & fees
20 Sept - 21 Sept
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 HK$863
HK$1,520 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$1,083
HK$1,813 total
includes taxes & fees
1 Oct - 2 Oct
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 HK$863
HK$1,555 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$902
HK$1,458 total
includes taxes & fees
15 Oct - 16 Oct
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 HK$1,396
HK$2,560 total
includes taxes & fees
27 Sept - 28 Sept
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 HK$1,451
HK$2,569 total
includes taxes & fees
21 Sept - 22 Sept
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, (11 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is HK$1,530
HK$1,982 total
includes taxes & fees
20 Sept - 21 Sept
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 HK$1,608
HK$2,933 total
includes taxes & fees
22 Sept - 23 Sept
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 HK$1,742
HK$3,102 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$1,059
HK$2,119 total
includes taxes & fees
1 Oct - 2 Oct
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 HK$1,274
HK$2,120 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$1,318
HK$2,427 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$1,702
HK$2,079 total
includes taxes & fees
27 Sept - 28 Sept
"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 HK$1,274
HK$2,103 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$527
HK$1,440 total
includes taxes & fees
21 Sept - 22 Sept
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 HK$1,137
HK$1,975 total
includes taxes & fees
23 Sept - 24 Sept
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 HK$902
HK$1,775 total
includes taxes & fees
20 Sept - 21 Sept
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 HK$777
HK$1,355 total
includes taxes & fees
4 Oct - 5 Oct
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Loved the room set up"
Tracy 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
203
Accommodation
179 Apartments
Lowest Price
HK$1,355
Highest Price
HK$3,102

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 24 apartments in Winchester for your trip. Take time to enjoy the array of shops and top-notch restaurants in this vibrant area.
Why should you consider an apartment versus a traditional hotel?
Often more spacious than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for solo travellers who want to stay in a quieter area.
What's the best apartment for my stay in Winchester?
Here is a favourite apartment in the area: Roadhaven1830: Located in Mount Jackson , 39.9 mi/64.2 km away. Includes free WiFi, a private garden and a Smart TV . Free parking and a terrace are on site .
How many apartments are there in Winchester?
Expedia has 24 apartments to book in Winchester.
What will the weather be like when I travel to Winchester?
Although 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 temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What should I see in Winchester?
Travellers 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 make your trip smoother 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 International Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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