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

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.
$170 nightly
The price is $193
Nov 2 - Nov 3
Total with taxes and fees
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.
$232 nightly
The price is $263
Oct 19 - Oct 20
Total with taxes and fees
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 traveler
$155 nightly
The price is $176
Nov 11 - Nov 12
Total with taxes and fees
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.
$243 nightly
The price is $253
Nov 2 - Nov 3
Total with taxes and fees
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.
$207 nightly
The price is $235
Nov 15 - Nov 16
Total with taxes and fees
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.
$268 nightly
The price is $304
Oct 18 - Oct 19
Total with taxes and fees
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
$289 nightly
The price is $328
Oct 18 - Oct 19
Total with taxes and fees
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.
$222 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
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.
$175 nightly
The price is $198
Nov 2 - Nov 3
Total with taxes and fees
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
$171 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
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.
$295 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
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.
$330 nightly
The price is $374
Oct 18 - Oct 19
Total with taxes and fees
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
$244 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
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
$263 nightly
The price is $288
Oct 20 - Oct 21
Total with taxes and fees
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.
$237 nightly
The price is $270
Oct 19 - Oct 20
Total with taxes and fees
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.
$245 nightly
The price is $263
Oct 18 - Oct 19
Total with taxes and fees
"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.
$302 nightly
The price is $332
Nov 3 - Nov 4
Total with taxes and fees
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
$244 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
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)
$120 nightly
The price is $135
Oct 28 - Oct 29
Total with taxes and fees
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.
$169 nightly
The price is $178
Oct 18 - Oct 19
Total with taxes and fees
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

Spark by Hilton Winchester

Spark by Hilton Winchester

8/10 Good
"It was a very pleasant stay with very helpful staff! I really wish it had added to my hilton honors points though."
Jennifer 2-night trip
Posted 4 hours ago
Spark by Hilton Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
152
Accommodation
185 Apartments
Lowest Price
$135
Highest Price
$374

Frequently asked questions

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

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