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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winchester apartments

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 traveler
The price is AED 367
AED 645 total
includes taxes & fees
1 Jul - 2 Jul
Cozy English Basement Apt quiet but close to downtown
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 AED 526
AED 1,039 total
includes taxes & fees
1 Jul - 2 Jul
Lunar Loft, with mountain views
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 AED 496
AED 859 total
includes taxes & fees
5 Jul - 6 Jul
Apple Mountain Retreat
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
10.0 out of 10, Exceptional, (11 reviews)
"Nice owner, great place"
United States
Leslie C.
The price is AED 502
AED 1,059 total
includes taxes & fees
1 Jul - 2 Jul
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 AED 544
AED 957 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 349
AED 771 total
includes taxes & fees
30 Jun - 1 Jul
The Queen of Winchester Three Bedroom with Upper Level Deck
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 AED 569
AED 953 total
includes taxes & fees
7 Jul - 8 Jul
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
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 AED 588
AED 1,112 total
includes taxes & fees
1 Jul - 2 Jul
Morocco Loft 2BR overlooking city walking mall
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 AED 507
AED 845 total
includes taxes & fees
9 Jul - 10 Jul
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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 AED 334
AED 1,159 total
includes taxes & fees
29 Jun - 30 Jun
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
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 AED 404
AED 728 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 797
AED 977 total
includes taxes & fees
5 Jul - 6 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 AED 680
AED 1,228 total
includes taxes & fees
29 Jun - 30 Jun
Nostalgia Lane in the heart of the city
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 AED 422
AED 712 total
includes taxes & fees
30 Jun - 1 Jul
The Blue Door steps from Handley Library
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 AED 753
AED 1,369 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 815
AED 1,448 total
includes taxes & fees
2 Jul - 3 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 AED 569
AED 941 total
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, (42 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 AED 362
AED 406 total
includes taxes & fees
6 Jul - 7 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, (63 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 AED 364
AED 658 total
includes taxes & fees
29 Jun - 30 Jun
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"The breakfast was the highlight of the stay. The lady staffing the breakfast area was just great!"
Christopher 1-night trip
Posted 2 hours ago
Quality Inn 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?
Below you'll find a top apartment in the area: Roadhaven1830: Located 39.9 mi/64.2 km away in Mount Jackson.
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 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 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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