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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 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, (30)
"The apartment is perfectly located by the trail and coffee shop and a cute restaurant! "
The price is AED 294
AED 584 total
includes taxes & fees
12 May - 13 May
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC
Historic apartment in Old Town Warrenton, Virginia
Outdoor dining

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (40)
"Host was amazing!"
The price is AED 621
AED 939 total
includes taxes & fees
6 May - 7 May
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, (77)
"We stay often. Consistently great place to stay while visiting family and friends in the leesburg area. "
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, (33)
"Amazing place to stay and perfect location in Harper's Ferry!"
The price is AED 558
AED 897 total
includes taxes & fees
6 May - 7 May
Best location! The Pullman Apt @ historic 1799 Inn
Family Farmhouse Inn
Garden

Family Farmhouse Inn

3.0 star property
9.6 out of 10, Exceptional, (34)
"Very nice , impeccable conditions , you will LOVE your stay."
The price is AED 474
AED 532 total
includes taxes & fees
6 May - 7 May
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)
"The perfect location from which to explore the town."
The price is AED 595
AED 950 total
includes taxes & fees
7 May - 8 May
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

9.4 out of 10, Exceptional, (3)
"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 647 total
includes taxes & fees
6 May - 7 May
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)
"Great stay"
The price is AED 466
AED 981 total
includes taxes & fees
5 May - 6 May
Dog-Friendly Downtown Studio — Walk to Park, Shops
New studio conveniently located in town of Luray.
Fridge, microwave, coffee/tea maker, electric kettle

New studio conveniently located in town of Luray.

9.8 out of 10, Exceptional, (55)
"Nice cozy stay short walk from restaurants and shops. Would stay again."
The price is AED 367
AED 678 total
includes taxes & fees
6 May - 7 May
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
8.8 out of 10, Excellent, (3)
"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, (17)
"Cute private apartment. Hot tub was amazing."
Epic Brunswick Apartment with Deck!
Cozy 1BR Apt Minutes From Skyline Drive!!
Fridge, microwave, oven, stovetop

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (28)
"Excellent stay! Great property. Looking gorward to a return stay."
The price is AED 496
AED 917 total
includes taxes & fees
5 May - 6 May
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, (7)
"The little red schoolhouse was adorably decorated, and very relaxing. We enjoyed the outside patio with the hot tub. We also cooked a great steak meal on the grill!!! Just the relaxing little Secluded weekend getaway we were looking for! "
The price is AED 511
AED 987 total
includes taxes & fees
5 May - 6 May
The Little Red Schoolhouse
Nostalgia Lane in the heart of the city
Miscellaneous

Nostalgia Lane in the heart of the city

9.4 out of 10, Exceptional, (8)
"We enjoyed the small town feel of Winchester. Our stay here was the cherry on top. Such a beautiful place with so much personality, we will definitely be back!!!!"
The price is AED 731
AED 1,303 total
includes taxes & fees
5 May - 6 May
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, (47)
"Awesome place if you enjoy the outdoors or just beautiful scenery"
Waterfront Virginia Retreat w/ Canoe, Pets Welcome
Berkeley Springs Haven w/ Sleepy Creek Access!

Berkeley Springs Haven w/ Sleepy Creek Access!

10.0 out of 10, Exceptional, (62)
"Perfect place to spend a cozy new year!"
Berkeley Springs Haven w/ Sleepy Creek Access!
Best location! The Iron Horse @ historic 1799 Inn
1 bedroom, free WiFi, bed sheets

Best location! The Iron Horse @ historic 1799 Inn

9.6 out of 10, Exceptional, (8)
"Cute place. Very clean. Perfect location to enjoy Harper’s Ferry."
The price is AED 650
AED 1,110 total
includes taxes & fees
5 May - 6 May
Best location! The Iron Horse @ historic 1799 Inn
Cozy English Basement Apt quiet but close to downtown
Miscellaneous

Cozy English Basement Apt quiet but close to downtown

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. "
The price is AED 331
AED 603 total
includes taxes & fees
5 May - 6 May
Cozy English Basement Apt quiet but close to downtown
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town
Smart TV

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

9.0 out of 10, Wonderful, (2)
"Susan was a great host. The location was convenient and the accomodation comfortable. "
The price is AED 551
AED 837 total
includes taxes & fees
7 May - 8 May
Charming 2-bedroom 2nd floor apartment with WiFi, AC in lovely Charles Town
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Exterior

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

9.0 out of 10, Wonderful, (4)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
The price is AED 753
AED 1,377 total
includes taxes & fees
5 May - 6 May
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, (313)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Great cabin. Clean and so welcoming"
The price is AED 1,062
AED 1,329 total
includes taxes & fees
28 May - 29 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (13)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
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?
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library: Neighborhood: Old Town Winchester. The Queen of Winchester Three Bedroom with Upper Level Deck: Amenities include private patios. Access to onsite laundry facilities is available on site.
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 Stonewall Jackson’s Headquarters 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.