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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester apartments

A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

1. 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 €176
includes taxes & fees
2 Nov - 3 Nov
Rosamond nice downtown studio apt
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

2. 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, (4 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 €240
includes taxes & fees
19 Oct - 20 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A wooden deck with wicker furniture, including two chairs and a small table with a candle.

3. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
8.8 out of 10, Excellent, (10 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 traveller
The price is €161
includes taxes & fees
11 Nov - 12 Nov
Cozy English Basement Apt quiet but close to downtown
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

4. 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 €225
includes taxes & fees
2 Nov - 3 Nov
The Queen of Winchester Three Bedroom with Upper Level Deck
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

5. 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 €213
includes taxes & fees
15 Nov - 16 Nov
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a sofa, ottoman, lamp, and a mirror.

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 €273
includes taxes & fees
18 Oct - 19 Oct
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

7. 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 €293
includes taxes & fees
18 Oct - 19 Oct
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

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, (14 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A building with a red door, white trim, and a small balcony with a metal railing.

9. 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 €181
includes taxes & fees
16 Nov - 17 Nov
The Stock Exchange downtown 3rd floor studio apt
A white building with a black door and a set of blue-painted stairs with black railings.

10. 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 €176
includes taxes & fees
27 Oct - 28 Oct
The Blue Door steps from Handley Library
A living room with a sofa, armchair, coffee table, and a television.

11. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 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 €296
includes taxes & fees
19 Oct - 20 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.

12. 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 €334
includes taxes & fees
18 Oct - 19 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A bedroom with a bed, bedside tables, a ceiling fan, and a window.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
Downtown Apt 2 • 2BR • Near Park & River • Private
A bedroom with a bed, two windows with curtains, a bedside table, a chair, and a door.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A fenced grassy field with a clear sky and distant hills.

15. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.4 out of 10, Exceptional, (13 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 €246
includes taxes & fees
19 Oct - 20 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.

16. "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 €241
includes taxes & fees
27 Oct - 28 Oct
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

17. 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.
The price is €304
includes taxes & fees
16 Nov - 17 Nov
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a framed picture on the wall.

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
Downtown Apt 3 • 2BR • Near Park & River • Private
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

19. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (52 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is €135
includes taxes & fees
26 Oct - 27 Oct
Roadhaven1830
A lake with clear water, surrounded by trees and a sandy shore.

20. 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 €162
includes taxes & fees
18 Oct - 19 Oct
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
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
"We really enjoyed our stay at the hotel. the room was clean, breakfast was good, staff very nice especially a special person by the name of Natalie. Really made our morning !!!!! She was especially nice, helpful and welcoming"
iris 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
152
Accommodation
173 Apartments
Lowest Price
€135
Highest Price
€334

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.