Search Apartments in Winchester

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Check prices for these dates

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28 Nov - 30 Nov
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5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
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16 Jan - 18 Jan

Apartments in Winchester

Exterior
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, (7)
"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
21 Dec - 22 Dec
Cozy English Basement Apt quiet but close to downtown
Interior
Rosamond nice downtown studio apt

Rosamond nice downtown studio apt

Winchester Historic District
8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
United States
John M.
The price is AED 404
AED 707 total
includes taxes & fees
23 Nov - 24 Nov
Rosamond nice downtown studio apt
Outdoor dining
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, (3)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is AED 446
AED 928 total
includes taxes & fees
22 Nov - 23 Nov
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Property grounds
Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!

Bluemont
8.8 out of 10, Excellent, (6)
"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 496
AED 992 total
includes taxes & fees
24 Nov - 25 Nov
Private apartment on a beautiful private farm!
Exterior detail
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Fauquier County
8.0 out of 10, Very Good, (1)
"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 367
AED 1,073 total
includes taxes & fees
1 Dec - 2 Dec
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fridge, microwave, oven, stovetop
The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt

2.0 star property
Winchester Historic District
6.0 out of 10, (1)
The price is AED 404
AED 728 total
includes taxes & fees
23 Nov - 24 Nov
The Stock Exchange downtown 3rd floor studio apt
Interior
Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm

Winchester
The price is AED 496
AED 847 total
includes taxes & fees
21 Nov - 22 Nov
Very charming & spacious 2 bedrm
Living area
Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall

2.0 star property
Old Town Winchester
10.0 out of 10, Exceptional, (2)
"Great property with all the comforts of home"
United States
Kristen R.
The price is AED 654
AED 1,190 total
includes taxes & fees
24 Nov - 25 Nov
Morocco Loft 2BR overlooking city walking mall
Exterior
Farm Suite at Valley View Farm

Farm Suite at Valley View Farm

2.0 star property
Delaplane
Farm Suite at Valley View Farm
Fridge, microwave, oven, stovetop
Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard

Old Town Winchester
9.0 out of 10, Wonderful, (2)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
The price is AED 536
AED 953 total
includes taxes & fees
1 Dec - 2 Dec
Yellow Submarine trendy basement apt and courtyard
3 bedrooms, iron/ironing board, WiFi, bed sheets
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, (14)
"Great location in the heart of Winchester. Walking distance to everything. "
United States
Andrew N.
The price is AED 679
AED 1,219 total
includes taxes & fees
23 Nov - 24 Nov
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
9.0 out of 10, Wonderful, (6)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is AED 753
AED 1,361 total
includes taxes & fees
23 Nov - 24 Nov
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Microwave, oven, stovetop, dishwasher
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Old Town Winchester
The price is AED 808
AED 1,432 total
includes taxes & fees
24 Nov - 25 Nov
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Terrace/patio
Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt

Old Town Winchester
9.6 out of 10, Exceptional, (5)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
The price is AED 815
AED 1,440 total
includes taxes & fees
30 Nov - 1 Dec
Scarborough Fair walk to downtown two story apt
Garden
Roadhaven 1830

Roadhaven 1830

3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (38)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
The price is AED 496
AED 557 total
includes taxes & fees
21 Nov - 22 Nov
Roadhaven 1830
Property grounds
Elegant Retreat w/Vintage Charm & Modern Comforts

Elegant Retreat w/Vintage Charm & Modern Comforts

Luray
9.6 out of 10, Exceptional, (5)
"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 AED 288
AED 488 total
includes taxes & fees
23 Nov - 24 Nov
Elegant Retreat w/Vintage Charm & Modern Comforts
Fridge, microwave, oven, stovetop
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, (15)
"Everything was great. Would stay again! Accurate listing."
United States
Marlin S.
The price is AED 360
AED 674 total
includes taxes & fees
23 Nov - 24 Nov
Loft Apt Just off C&O near Harpers Ferry and AT
Outdoor dining
The San Francisco Way

The San Francisco Way

Martinsburg
9.4 out of 10, Exceptional, (3)
"Super cute, great spot, affordable. Would stay again if I visit Martinsburg. "
United States
Alex R.
The price is AED 309
AED 682 total
includes taxes & fees
22 Nov - 23 Nov
The San Francisco Way
1 bedroom, desk, WiFi
Dog-Friendly Downtown Studio — Walk to Park, Shops

Dog-Friendly Downtown Studio — Walk to Park, Shops

2.0 star property
Luray
10.0 out of 10, Exceptional, (9)
"We had a great stay at this pet friendly spot! We were in the area to visit family, and the location was perfect. "
United States
Roberta B.
The price is AED 345
AED 816 total
includes taxes & fees
25 Nov - 26 Nov
Dog-Friendly Downtown Studio — Walk to Park, Shops
Exterior
New studio conveniently located in town of Luray.

New studio conveniently located in town of Luray.

Luray
9.8 out of 10, Exceptional, (74)
"It's absolutely amazing will definitely come back again location was perfect"
United States
Warren R.
The price is AED 349
AED 656 total
includes taxes & fees
22 Nov - 23 Nov
New studio conveniently located in town of Luray.
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"The best hotel in Winchester! Had the most pleasant stay, everything was perfect. The room was super clean, as well as the other areas of the hotel. Had a delicious breakfast with lots of options. The front desk staff was very friendly and accommodating. Will stay again!"
Renee 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 27 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: Roadhaven 1830: Situated in Mount Jackson, 39.9 mi/64.2 km from the heart of Winchester.
How many apartments can I expect to find in Winchester?
Expedia has 27 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.