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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchester apartments

A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

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 £202
includes taxes & fees
4 Oct - 5 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

2. 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 £189
includes taxes & fees
5 Oct - 6 Oct
The Queen of Winchester Three Bedroom with Upper Level Deck
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

3. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is £149
includes taxes & fees
6 Oct - 7 Oct
Rosamond nice downtown studio apt
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

4. 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 £181
includes taxes & fees
4 Oct - 5 Oct
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a sofa, ottoman, lamp, and a mirror.

5. 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 £234
includes taxes & fees
4 Oct - 5 Oct
Morocco Loft 2BR overlooking city walking mall
A white building with a black door and a set of blue-painted stairs with black railings.

6. 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 £149
includes taxes & fees
4 Oct - 5 Oct
The Blue Door steps from Handley Library
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

7. 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, (13 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is £187
includes taxes & fees
4 Oct - 5 Oct
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

8. 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 £263
includes taxes & fees
18 Oct - 19 Oct
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A living room with a sofa, armchair, coffee table, and a television.

9. 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, (19 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 £254
includes taxes & fees
4 Oct - 5 Oct
Nostalgia Lane in the heart of the city
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

10. 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 £284
includes taxes & fees
4 Oct - 5 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

11. 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 £303
includes taxes & fees
4 Oct - 5 Oct
Scarborough Fair walk to downtown two story apt
A bedroom with a bed, two windows with curtains, a bedside table, a chair, and a door.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is £242
includes taxes & fees
4 Oct - 5 Oct
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A bedroom with a bed, a nightstand, a window with curtains, and a door.

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
The price is £236
includes taxes & fees
4 Oct - 5 Oct
Downtown Apt 3 • 2BR • Near Park & River • Private
A fenced grassy field with a clear sky and distant hills.

14. 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 £206
includes taxes & fees
5 Oct - 6 Oct
Lunar Loft, with mountain views
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

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 £204
includes taxes & fees
4 Oct - 5 Oct
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A bedroom with a bed, bedside tables, a ceiling fan, and a window.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is £208
includes taxes & fees
1 Nov - 2 Nov
Downtown Apt 2 • 2BR • Near Park & River • Private
A lake with clear water, surrounded by trees and a sandy shore.

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 £132
includes taxes & fees
4 Oct - 5 Oct
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

18. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (51 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is £95
includes taxes & fees
14 Oct - 15 Oct
Roadhaven1830
A tented accommodation with a wooden deck and a view of the surrounding forest.

19. Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
9.6 out of 10, Exceptional, (9 reviews)
"Wonderful stay! Will be back! "
United States
Shanna A.
The price is £277
includes taxes & fees
5 Oct - 6 Oct
Glamping dome w/ hot tub & mountain views
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

20. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (60 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is £177
includes taxes & fees
1 Nov - 2 Nov
Best location! The Pullman Apt @ historic 1799 Inn
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

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent
"Stayed here one night for a biz trip and was very pleased with the experience!! Quiet, clean, and a very comfortable bed. Tons of outlets available which was great because I had to tech check some gear and charge a bunch of batteries. They had a breakfast area but we did not have anything. Looked nice though. Historic downtown Harpers Ferry is a 4 min drive. We were able to spend 1.5hrs walking around and taking in some scenery. Beautiful town with lots of stores that were actually open on a Tuesday midday. Looking forward to visiting in the future with my family. Will definitely stay at this hotel again!!"
Benjamin 1-night trip
Posted less than an hour ago
Quality Inn Harpers Ferry - Charles Town

Find out more about Winchester

Winchester Apartments information

Number of reviews
191
Accommodation
173 Apartments
Lowest Price
£95
Highest Price
£303

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 23 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?
Below you'll find a favourite apartment in the area: Roadhaven1830: Located in Mount Jackson , 39.9 mi/64.2 km from the heart of Winchester. 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 23 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.