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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 171 Apartments in Winchester with updated reviews, rates, and availability.

Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC
Fridge, microwave, oven, stovetop

Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

9.8 out of 10, Exceptional, (26)
"The location was perfect. The host were very prompt with any questions. Everything was very clean and all essentials at hand. Would come back if in the area. "
The price is AED 294
AED 584 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC
Historic apartment in Old Town Warrenton, Virginia
Interior

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (37)
"Great location and comfortable place."
The price is AED 606
AED 915 total
includes taxes & fees
17 Apr - 18 Apr
Historic apartment in Old Town Warrenton, Virginia
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues
Fridge, microwave, oven, stovetop

Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

10.0 out of 10, Exceptional, (75)
"Clean, quiet, and cozy. Thank you for being such great hosts—we really enjoyed our stay!!"
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues
Best location! The Pullman Apt @ historic 1799 Inn
Property grounds

Best location! The Pullman Apt @ historic 1799 Inn

9.4 out of 10, Exceptional, (32)
"We had such a great time in Harper’s Ferry and at the 1799 Inn. A perfect location to hang out in the town and hike. "
The price is AED 558
AED 909 total
includes taxes & fees
20 Apr - 21 Apr
Best location! The Pullman Apt @ historic 1799 Inn
Family Farmhouse Inn
Garden

Family Farmhouse Inn

3.0 star property
9.4 out of 10, Exceptional, (33)
"Very nice management "
The price is AED 474
AED 532 total
includes taxes & fees
17 Apr - 18 Apr
Family Farmhouse Inn
Best location! The Ohio Suite @ historic 1799 Inn
1 bedroom, free WiFi, bed sheets

Best location! The Ohio Suite @ historic 1799 Inn

10.0 out of 10, Exceptional, (12)
"Park your car and walk to all the wonderful sites that town has to offer. My fiancé loved watching the trains come and go, and they did not wake us through the night. The outlets in the living room didn't work, but that wasn't a big enough deal to remove a star. The rocking chairs on the porch were so comfortable, and it was great to have a free reserved parking spot since it costs 20 and is difficult to get a public spot later in the day to tour. Within two blocks, you have several options...
The price is AED 595
AED 966 total
includes taxes & fees
23 Apr - 24 Apr
Best location! The Ohio Suite @ historic 1799 Inn
The Queen of Winchester Three Bedroom with Upper Level Deck
Private kitchen

The Queen of Winchester Three Bedroom with Upper Level Deck

10.0 out of 10, Exceptional, (2)
"Enjoyed our stay. 5 minute drive to historic downtown. Property owner was accommodating and easy to communicate with. Very nice stay while working in Winchester. "
The price is AED 246
AED 643 total
includes taxes & fees
17 Apr - 18 Apr
The Queen of Winchester Three Bedroom with Upper Level Deck
Dog-Friendly Downtown Studio — Walk to Park, Shops
1 bedroom, desk, WiFi

Dog-Friendly Downtown Studio — Walk to Park, Shops

2.0 star property
10.0 out of 10, Exceptional, (4)
"Stayed one night with my dog. Nice studio with easy parking right out front. Very convenient location just a short drive to Shenandoah National Park!"
The price is AED 353
AED 808 total
includes taxes & fees
21 Apr - 22 Apr
Dog-Friendly Downtown Studio — Walk to Park, Shops
New studio conveniently located in town of Luray.
Exterior

New studio conveniently located in town of Luray.

9.8 out of 10, Exceptional, (55)
"This was a clean and conveniently located stay while we visited Shenandoah. A lovely cottage with several notes left in places where one may have questions. We were very happy in our little cottage and it was very close to all of the restaurants and shops in Luray!"
The price is AED 367
AED 678 total
includes taxes & fees
28 Apr - 29 Apr
New studio conveniently located in town of Luray.
Front Royal Retreat on 3 Acres w/ Mtn Views!
Fridge, microwave, oven, dishwasher

Front Royal Retreat on 3 Acres w/ Mtn Views!

2.0 star property
10.0 out of 10, Exceptional, (2)
"House and overall property was very clean and we really enjoyed it and the spring water was amazing"
Front Royal Retreat on 3 Acres w/ Mtn Views!
Epic Brunswick Apartment with Deck!
1 bedroom, desk, iron/ironing board, WiFi

Epic Brunswick Apartment with Deck!

9.8 out of 10, Exceptional, (16)
"Cute private apartment. Hot tub was amazing."
Epic Brunswick Apartment with Deck!
Cozy 1BR Apt Minutes From Skyline Drive!!
Smart TV

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (28)
"Property is short drive from family and our favorite place to stay when visiting the area. Hosts are incredibly accommodating and it's a pet friendly property!"
The price is AED 496
AED 913 total
includes taxes & fees
17 Apr - 18 Apr
Cozy 1BR Apt Minutes From Skyline Drive!!
The Little Red Schoolhouse
Fridge, microwave, oven, stovetop

The Little Red Schoolhouse

9.8 out of 10, Exceptional, (6)
"all the modern amenities in a 1920s one room school house"
The price is AED 364
AED 795 total
includes taxes & fees
27 Apr - 28 Apr
The Little Red Schoolhouse
Nostalgia Lane in the heart of the city
3 bedrooms, iron/ironing board, WiFi, bed sheets

Nostalgia Lane in the heart of the city

9.0 out of 10, Wonderful, (6)
"The apartment has an eclectic layout with great charm. Very clean and perfectly situated to Old Town. "
The price is AED 731
AED 1,298 total
includes taxes & fees
20 Apr - 21 Apr
Nostalgia Lane in the heart of the city
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Property grounds

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

10.0 out of 10, Exceptional, (46)
"Fun little place to base from. Especially enjoyed the water and fire pit."
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Berkeley Springs Haven w/ Sleepy Creek Access!
Exterior

Berkeley Springs Haven w/ Sleepy Creek Access!

10.0 out of 10, Exceptional, (62)
"Everything was wonderful. The property was beautiful. There were other people staying at the homes on site, but none of it was a distraction. Close enough to town to do excursions. The only thing I would add is maybe a screen door so that you could allow some extra fresh air in and light. Hosts were wonderful and easy to contact when we needed something. Recommend for a cozy gate away."
Berkeley Springs Haven w/ Sleepy Creek Access!
Best location! The Iron Horse @ historic 1799 Inn
Property grounds

Best location! The Iron Horse @ historic 1799 Inn

9.6 out of 10, Exceptional, (8)
"The property was within walking distance to everything. Very clean, updated, everything you need. Great communication with owner"
The price is AED 650
AED 1,113 total
includes taxes & fees
27 Apr - 28 Apr
Best location! The Iron Horse @ historic 1799 Inn
Cozy English Basement Apt quiet but close to downtown
Exterior

Cozy English Basement Apt quiet but close to downtown

9.4 out of 10, Exceptional, (6)
"Very cute place to stay at a perfect location to the little historic district of Winchester. Bed was comfortable but very small futon. We are tall people so it was not quite long enough for us. Bathroom was extremely small, doable for us but if we were bigger people it would be difficult to get into that space. Water pressure for sink was poor, shower was just okay. Quaint place with a friendly, engaged owner. We would go back just for the amazing location!"
The price is AED 331
AED 603 total
includes taxes & fees
20 Apr - 21 Apr
Cozy English Basement Apt quiet but close to downtown
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town
2 bedrooms, desk, WiFi, bed sheets

Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town

9.0 out of 10, Wonderful, (2)
"My aunt and I stayed here for a few nights and really enjoyed our stay. The space is huge, cozy, and private being the only apartment above the convenience store. It's a 1 minute drive from shopping in Charles Town and a short drive to Harpers Ferry and Shepherdstown. It was clean, and the hosts were generous even when we had a few very minor issues during our stay. They helped us through it and were very communicative. I would recommend this place to angone."
The price is AED 551
AED 845 total
includes taxes & fees
17 Apr - 18 Apr
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Property grounds

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

9.0 out of 10, Wonderful, (4)
"We really like staying walking distance from the Historic District in Winchester and this was a great home base to do so. The whole process was seemless and easy. I will most likley try to come back for my conference next year. The place is clean and comfortable. Fun times "
The price is AED 753
AED 1,353 total
includes taxes & fees
17 Apr - 18 Apr
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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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Other property types in Winchester

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (311)
"This lovely cabin was exactly what we were looking for. It's cozy with a spectacular view and the river access was perfectly scenic. "
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Smart TV, fireplace, books

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Lovely cabin, very clean and well maintained. A girlfriend weekend and we wanted a great place to hang out and this fit the bill. We never got the TV to work but could be user error. "
The price is AED 1,062
AED 1,321 total
includes taxes & fees
30 Apr - 1 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (97)
"We stayed for 2 nights fishing, and site seeing get away. It was the perfect location!"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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.

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 22 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 top apartment in the area: Family Farmhouse Inn: It’s situated in Mount Jackson, 39.9 mi/64.2 km from Winchester.
How many apartments can I expect to find in Winchester?
Expedia has 22 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.