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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester apartments

A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

1. Executive Suites

Executive Suites
3.0 star property
Winchester
$252 nightly
The price is $286
Nov 10 - Nov 11
Total with taxes and fees
Executive Suites
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.
$158 nightly
The price is $179
Nov 12 - Nov 13
Total with taxes and fees
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.
$220 nightly
The price is $237
Nov 29 - Nov 30
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

4. 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
8.8 out of 10, Excellent, (5 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.
$213 nightly
The price is $241
Nov 19 - Nov 20
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
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.
$190 nightly
The price is $215
Nov 15 - Nov 16
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A building with a red door, white trim, and a small balcony with a metal railing.

6. 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.
$163 nightly
The price is $185
Nov 12 - Nov 13
Total with taxes and fees
The Stock Exchange downtown 3rd floor studio apt
A living room with a sofa, ottoman, lamp, and a mirror.

7. 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.
$246 nightly
The price is $279
Nov 10 - Nov 11
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.

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
$266 nightly
The price is $302
Nov 10 - Nov 11
Total with taxes and fees
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
9.0 out of 10, Wonderful, (22 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
$270 nightly
The price is $306
Nov 15 - Nov 16
Total with taxes and fees
Nostalgia Lane in the heart of the city
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a table and chairs.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
$259 nightly
The price is $284
Nov 10 - Nov 11
Total with taxes and fees
Downtown Apt 2 • 2BR • Near Park & River • Private
A modern kitchen with a wooden floor, a large window, and a kitchen island with stools.

11. 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.
$220 nightly
The price is $251
Nov 10 - Nov 11
Total with taxes and fees
Lunar Loft, with mountain views
A wooden bridge leading to a house surrounded by lush greenery and purple flowers.

12. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
9.8 out of 10, Exceptional, (15 reviews)
"Nice owner, great place"
United States
Leslie C.
$275 nightly
The price is $313
Nov 11 - Nov 12
Total with taxes and fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

13. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
9.6 out of 10, Exceptional, (5 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.
$264 nightly
The price is $283
Nov 10 - Nov 11
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A black door with the number 415, a window, and a hanging flower basket.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Perfect for a quick stay over when going to shenedoah natl park. Location is awesome. Very clean and spacious! Highly recommend!"
United States
Maureen N.
$260 nightly
The price is $285
Nov 12 - Nov 13
Total with taxes and fees
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A living room with a dining table, two sofas, a floor lamp, a clock, and a window with curtains.

15. 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.
$241 nightly
The price is $265
Nov 12 - Nov 13
Total with taxes and fees
Downtown Apt 3 • 2BR • Near Park & River • Private
A small wooden cabin with a porch, surrounded by trees.

16. 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.
$156 nightly
The price is $164
Nov 10 - Nov 11
Total with taxes and fees
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.

17. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.4 out of 10, Exceptional, (55 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
$124 nightly
The price is $139
Nov 12 - Nov 13
Total with taxes and fees
Roadhaven1830
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (62 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
$190 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

19. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
10.0 out of 10, Exceptional, (71 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
$157 nightly
The price is $166
Nov 12 - Nov 13
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A hot tub with a wooden deck and a tented accommodation.

20. Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful stay! Will be back! "
United States
Shanna A.
$374 nightly
The price is $405
Dec 7 - Dec 8
Total with taxes and fees
Glamping dome w/ hot tub & mountain views
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

Skyland

Skyland

10/10 Excellent
"All was very nice no complaints."
Donald 1-night trip
Posted less than an hour ago
Skyland

Find out more about Winchester

Winchester Apartments information

Number of reviews
272
Accommodation
185 Apartments
Lowest Price
$139
Highest Price
$405

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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