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

Search Apartments in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester apartments

Terrace/patio

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)
"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
The price is AED 367
AED 645 total
includes taxes & fees
16 Aug - 17 Aug
Cozy English Basement Apt quiet but close to downtown
Fridge, microwave, oven, stovetop

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 AED 360
AED 1,026 total
includes taxes & fees
19 Aug - 20 Aug
The Queen of Winchester Three Bedroom with Upper Level Deck
Interior

3. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is AED 404
AED 716 total
includes taxes & fees
25 Aug - 26 Aug
Rosamond nice downtown studio apt
Smart TV, books

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 AED 507
AED 870 total
includes taxes & fees
31 Aug - 1 Sep
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Interior

5. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is AED 477
AED 807 total
includes taxes & fees
30 Aug - 31 Aug
Pretty Little Apt by the Train II
TV

6. 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 AED 544
AED 965 total
includes taxes & fees
17 Aug - 18 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Exterior detail

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 AED 404
AED 737 total
includes taxes & fees
25 Aug - 26 Aug
The Stock Exchange downtown 3rd floor studio apt
Private kitchen

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, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is AED 716
AED 928 total
includes taxes & fees
31 Aug - 1 Sep
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Smart TV

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, (18 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 AED 679
AED 1,194 total
includes taxes & fees
16 Aug - 17 Aug
Nostalgia Lane in the heart of the city
Smart TV

10. Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is AED 536
AED 957 total
includes taxes & fees
16 Aug - 17 Aug
Yellow Submarine trendy basement apt and courtyard
Private kitchen

11. 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 AED 691
AED 1,298 total
includes taxes & fees
31 Aug - 1 Sep
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Dining

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 AED 753
AED 1,382 total
includes taxes & fees
16 Aug - 17 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Property grounds

13. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is AED 340
AED 803 total
includes taxes & fees
17 Aug - 18 Aug
Lunar Loft, with mountain views
Smart TV, fireplace

14. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is AED 815
AED 1,461 total
includes taxes & fees
23 Aug - 24 Aug
Scarborough Fair walk to downtown two story apt
Property grounds

15. 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, (12 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is AED 446
AED 990 total
includes taxes & fees
24 Aug - 25 Aug
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Outdoor dining

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 AED 797
AED 977 total
includes taxes & fees
25 Aug - 26 Aug
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Interior

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 AED 437
AED 1,284 total
includes taxes & fees
7 Sep - 8 Sep
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Beach

18. 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, (2 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 AED 247
AED 674 total
includes taxes & fees
16 Aug - 17 Aug
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Desk, iron/ironing board, WiFi (free), bed sheets

19. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.8 out of 10, Exceptional, (28 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
The price is AED 551
AED 1,005 total
includes taxes & fees
16 Aug - 17 Aug
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Lobby

20. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (47 reviews)
"Quiet, recently renovated and very cute suite with thoughtful accommodations. The owner was very nice and pleasant 😊We stayed in the Elizabeth suite and would definitely stay again!"
United States
Martine
The price is AED 533
AED 598 total
includes taxes & fees
17 Aug - 18 Aug
Roadhaven1830
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"The room was finished vinyl wood grain floors which an improvement over carpeting in rooms from previousstays, very nice, considering pet friendly hotel. Bathroom clean but walls could use some new finish as just painted white, little tacky looking. Bed comfortable with plenty of pillows for proping up to watch tv or just sleeping. Staff friendly at check in and at breakfast. Will stay again"
Peter 1-night trip
Posted 12 hours ago
Travelodge by Wyndham Winchester

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 26 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 26 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. Stonewall Jackson's Headquarters 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.