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

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
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winchester apartments

Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stayed "
United States
Mike F.
The price is AU$329
includes taxes & fees
29 July - 30 July
Apple Mountain Retreat
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 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 AU$254
includes taxes & fees
29 July - 30 July
Cozy English Basement Apt quiet but close to downtown
Smart TV, books

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
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is AU$335
includes taxes & fees
29 July - 30 July
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
TV

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, (1 review)
The price is AU$372
includes taxes & fees
26 July - 27 July
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Fridge, microwave, oven, stovetop

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 AU$316
includes taxes & fees
29 July - 30 July
The Queen of Winchester Three Bedroom with Upper Level Deck
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is AU$451
includes taxes & fees
29 July - 30 July
Morocco Loft 2BR overlooking city walking mall
Private kitchen

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, (7 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is AU$356
includes taxes & fees
29 July - 30 July
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Property grounds

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 AU$419
includes taxes & fees
12 Aug - 13 Aug
Lunar Loft, with mountain views
Private kitchen

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 AU$490
includes taxes & fees
31 July - 1 Aug
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Smart TV

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, (17 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 AU$471
includes taxes & fees
19 July - 20 July
Nostalgia Lane in the heart of the city
Property grounds

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 AU$439
includes taxes & fees
11 Aug - 12 Aug
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Outdoor dining

"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, (3 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 AU$374
includes taxes & fees
29 July - 30 July
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Smart TV, fireplace

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)
"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "
United States
Larry E.
The price is AU$551
includes taxes & fees
19 July - 20 July
Scarborough Fair walk to downtown two story apt
Dining

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 AU$531
includes taxes & fees
20 July - 21 July
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Smart TV

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 AU$369
includes taxes & fees
26 July - 27 July
Yellow Submarine trendy basement apt and courtyard
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (44 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back "
United States
Varnell
The price is AU$225
includes taxes & fees
28 July - 29 July
Roadhaven1830
Exterior

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (25 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
The price is AU$290
includes taxes & fees
21 July - 22 July
Beautiful, Historic, Hiking, Biking and C&O Canal
Interior

Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (20 reviews)
"The place was nice and cozy"
United States
Andrew E.
The price is AU$295
includes taxes & fees
22 July - 23 July
Loft Apt Just off C&O near Harpers Ferry and AT
Outdoor dining

The Downtown Flat at Creekside

The Downtown Flat at Creekside
Berkeley Springs
10.0 out of 10, Exceptional, (21 reviews)
"It was beautifully decorated, cozy and within walking distance of most attractions. "
United States
Tricia M.
The price is AU$426
includes taxes & fees
30 July - 31 July
The Downtown Flat at Creekside
Property grounds

Quiet suite w/ outdoor furniture

Quiet suite w/ outdoor furniture
Luray
9.8 out of 10, Exceptional, (7 reviews)
"The Legacy Inn in Luray was great! Easy to find, easy entry (with a code), within walking distance of dining and outdoor music, and an easy drive to Luray Caverns and Shenandoah National Park. Highly recommend."
United States
Robert
The price is AU$243
includes taxes & fees
23 July - 24 July
Quiet suite w/ outdoor furniture
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"It was very quiet and clean, great place to stay!"
Wendy 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
229
Accommodation
194 Apartments
Lowest Price
AU$225
Highest Price
AU$551

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 25 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 25 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 Winchester Little 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.