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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

10.0 out of 10, Exceptional, (24)
"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
30 Mar - 31 Mar
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, (36)
"This adorable home was perfect for two adult family members to make delightful memories and reconnect considering the somber circumstances. Flexible configuration will meet the needs from young family to girlfriend weekend away: Highly recommend!"
The price is AED 606
AED 915 total
includes taxes & fees
30 Mar - 31 Mar
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, (73)
"We are repeat guests. We love the place!"
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, (30)
"Perfect spot.for Harpers.Ferry. it was winter and a little cold inside. "
The price is AED 558
AED 909 total
includes taxes & fees
27 Mar - 28 Mar
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, (32)
"Very nice management "
The price is AED 474
AED 532 total
includes taxes & fees
16 Apr - 17 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 958 total
includes taxes & fees
30 Mar - 31 Mar
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, (1)
"If you want to be in the town and have quick access to everything, this is the place for you."
The price is AED 242
AED 639 total
includes taxes & fees
22 Apr - 23 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, (2)
"Great stay"
The price is AED 331
AED 799 total
includes taxes & fees
1 Apr - 2 Apr
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)
"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
1 Apr - 2 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!!
Fridge, microwave, oven, stovetop

Cozy 1BR Apt Minutes From Skyline Drive!!

9.6 out of 10, Exceptional, (26)
"I love this property! An oasis for me and my dog. Jimmie is a great host, as well!"
The price is AED 496
AED 901 total
includes taxes & fees
27 Mar - 28 Mar
Cozy 1BR Apt Minutes From Skyline Drive!!
The Little Red Schoolhouse
Fridge, microwave, oven, stovetop

The Little Red Schoolhouse

9.4 out of 10, Exceptional, (3)
"What a wonderful place to relax and unwind. Great location with a beautiful view."
The price is AED 364
AED 795 total
includes taxes & fees
13 Apr - 14 Apr
The Little Red Schoolhouse
Nostalgia Lane in the heart of the city
Miscellaneous

Nostalgia Lane in the heart of the city

9.6 out of 10, Exceptional, (4)
"We need overnight accommodations for our daughter’s surprise proposal. We checked into the VRBO and we were stunned! We walked around in silence taking in all of the charm, beauty and uniqueness of this home. This is a clean place with a very comfortable mattress! It is a fascinating place and we just loved it!! The host was very gracious and communicative - we wanted for nothing!! Five Starts "
The price is AED 731
AED 1,265 total
includes taxes & fees
27 Mar - 28 Mar
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, (45)
"This was a quiet, scenic and well appointed property. Our host was even kind enough to offer assistance when my car needed a jump. Something she found was happening from the neighbor. Great sense of community, great hospitality. The cows on the adjacent property behind the creek would walk down and graze and drink from the creek. It was magic. Thank you again. "
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, (61)
"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)
"The property was within walking distance to everything. Very clean, updated, everything you need. Great communication with owner"
The price is AED 650
AED 1,117 total
includes taxes & fees
27 Mar - 28 Mar
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

9.4 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
27 Mar - 28 Mar
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

10.0 out of 10, Exceptional, (1)
"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 849 total
includes taxes & fees
27 Mar - 28 Mar
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)
"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 1,340 total
includes taxes & fees
27 Mar - 28 Mar
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, (307)
"I recently stayed at this cabin over the weekend, and it was an unforgettable experience. The views were absolutely breathtaking — whether it was sunrise over the mountains or relaxing in the evening with a stunning sunset, the scenery was incredible from every angle.The cabin itself was just as impressive. It was beautifully designed, immaculately clean, and had all the comforts of home. From cozy furniture to thoughtful amenities, everything was perfect. The peaceful surroundings made it the...
Star view cabin-Riverfront
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
2 bedrooms, WiFi, bed sheets

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (343)
"Amazing view, and very quiet. Exactly what i was looking for. "
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (36)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
The price is AED 1,062
AED 1,302 total
includes taxes & fees
24 Apr - 25 Apr
Dreamtime - Modern A-frame Cabin w/ Hot tub
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 21 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: 39.9 mi/64.2 km away in Mount Jackson.
How many apartments can I expect to find in Winchester?
Expedia has 21 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.