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

Apartments in Winchester

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchester apartments

A wooden deck with wicker furniture, including two chairs and a small table with a candle.

1. 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)
"Great location and extremely easy in and out. Cute and clever little apartment. Quirky kitchen set up, but absolutely everything was provided, and I cooked 9 out of 10 nights."
United States
Wayne C.
Cozy English Basement Apt quiet but close to downtown
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

2. 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 NZ$339
includes taxes & fees
12 Nov - 13 Nov
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

3. 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 NZ$442
includes taxes & fees
28 Oct - 29 Oct
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.

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 NZ$404
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.

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 NZ$573
includes taxes & fees
26 Oct - 27 Oct
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

6. 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 NZ$569
includes taxes & fees
25 Oct - 26 Oct
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A building with a red door, white trim, and a small balcony with a metal railing.

7. 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 NZ$349
includes taxes & fees
12 Nov - 13 Nov
The Stock Exchange downtown 3rd floor studio apt
A room with a radiator, a wooden rocking chair, a door, and a window with a lace curtain.

8. 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 NZ$339
includes taxes & fees
5 Nov - 6 Nov
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.

9. 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, (15 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is NZ$601
includes taxes & fees
5 Nov - 6 Nov
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A living room with a sofa, armchair, coffee table, and a television.

10. 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 NZ$574
includes taxes & fees
1 Nov - 2 Nov
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.

11. 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 NZ$655
includes taxes & fees
26 Oct - 27 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a framed picture on the wall.

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"This property is absolutely perfect: great location for walking through the historic part of town, close to food & fun, very well appointed (right down to quality toilet paper!) & perfectly clean. Yuliya responded very quickly from the moment I made the reservation to checkout. We would stay again for sure! Thank you, Yuliya & Mark!"
United States
kim B.
The price is NZ$470
includes taxes & fees
26 Oct - 27 Oct
Downtown Apt 3 • 2BR • Near Park & River • Private
A mountainous landscape with rolling hills and dense forest.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is NZ$498
includes taxes & fees
25 Oct - 26 Oct
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A modern kitchen with a wooden floor, a large window, and a kitchen island with stools.

14. 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 NZ$475
includes taxes & fees
26 Oct - 27 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 NZ$462
includes taxes & fees
28 Oct - 29 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.

16. 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 NZ$580
includes taxes & fees
16 Nov - 17 Nov
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A bedroom with a bed, a nightstand, a ceiling fan, and a bathroom visible through an open door.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is NZ$470
includes taxes & fees
26 Oct - 27 Oct
Downtown Apt 2 • 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.

18. 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 NZ$235
includes taxes & fees
26 Oct - 27 Oct
Roadhaven1830
A small wooden cabin with a porch, surrounded by trees.

19. 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 NZ$310
includes taxes & fees
25 Oct - 26 Oct
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

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, (70 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 NZ$315
includes taxes & fees
25 Oct - 26 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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Front desk upgraded our room so we could fit our bikes in the room. Bed was too soft. Otherwise room was nice. Breakfast was good."
Jenny 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Winchester, VA

Find out more about Winchester

Winchester Apartments information

Number of reviews
224
Accommodation
185 Apartments
Lowest Price
NZ$235
Highest Price
NZ$655

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.