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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Winchester apartments

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 £209
includes taxes & fees
7 Jul - 8 Jul
Lunar Loft, with mountain views
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 £135
includes taxes & fees
6 Jul - 7 Jul
Cozy English Basement Apt quiet but close to downtown
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 £159
includes taxes & fees
5 Jul - 6 Jul
The Queen of Winchester Three Bedroom with Upper Level Deck
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.
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
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 £195
includes taxes & fees
3 Aug - 4 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stayed "
United States
Mike F.
The price is £178
includes taxes & fees
5 Jul - 6 Jul
Apple Mountain Retreat
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 £242
includes taxes & fees
3 Aug - 4 Aug
Morocco Loft 2BR overlooking city walking mall
Fridge, microwave, oven, stovetop

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Very enjoyable stay right in historical Winchester. We enjoyed walking to a German restaurant for dinner and rested well. "
United States
Brad E.
The price is £198
includes taxes & fees
7 Jul - 8 Jul
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
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 £180
includes taxes & fees
8 Jul - 9 Jul
Dreamweaver — 1BR 1BA just two blocks from the downtown 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, (6 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is £187
includes taxes & fees
17 Jul - 18 Jul
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Interior

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very good, (1 review)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
The price is £260
includes taxes & fees
3 Aug - 4 Aug
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Exterior detail

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 £169
includes taxes & fees
4 Jul - 5 Jul
The Blue Door steps from Handley Library
Exterior detail

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 £153
includes taxes & fees
15 Jul - 16 Jul
The Stock Exchange downtown 3rd floor studio apt
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 £203
includes taxes & fees
17 Jul - 18 Jul
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
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 £251
includes taxes & fees
15 Jul - 16 Jul
Nostalgia Lane in the heart of the city
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
9.2 out of 10, Wonderful, (9 reviews)
"Great location…"
United States
John P.
The price is £268
includes taxes & fees
3 Aug - 4 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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 £284
includes taxes & fees
15 Jul - 16 Jul
Scarborough Fair walk to downtown two story apt
Private kitchen

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Winchester
The price is £197
includes taxes & fees
7 Jul - 8 Jul
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (43 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 £83
includes taxes & fees
10 Jul - 11 Jul
Roadhaven1830
Exterior

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, (64 reviews)
"The apartment was cozy and just as described. Check-in was super easy and the owners were very responsive to any questions we had. Thanks for a super pleasant stay!"
United States
Candi M.
The price is £137
includes taxes & fees
7 Jul - 8 Jul
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

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"We stayed here for a wedding nearby, it was great"
Rosa 2-night trip
Posted 10 hours ago
Courtyard by Marriott Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
228
Accommodation
197 Apartments
Lowest Price
£83
Highest Price
£284

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 26 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?
Here's a popular apartment in the area: Roadhaven1830: Located 39.9 mi/64.2 km away in Mount Jackson .
How many apartments are there in Winchester?
Expedia has 26 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 Winchester Little Theater, 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.