Apartments in Winchester for Rent

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Our top choices for Winchester apartments

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 ¥21,553
¥36,982 total
includes taxes & fees
Jun 9 - Jun 10
Apple Mountain Retreat

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 ¥22,032
¥37,625 total
includes taxes & fees
Jun 4 - Jun 5
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (9 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 ¥21,553
¥42,772 total
includes taxes & fees
Jun 8 - Jun 9
Lunar Loft, with mountain views

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 ¥26,821
¥45,944 total
includes taxes & fees
Jun 11 - Jun 12
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

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, (16 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is ¥29,535
¥52,276 total
includes taxes & fees
Jun 9 - Jun 10
Nostalgia Lane in the heart of the city

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)
"Our stay was great, and we had an excellent time in the area. Short drive to hiking spots and within walking distance to the local Bluemont Station restaurant. Highly recommend this stay in a quaint location!"
United States
Nicholas B.
The price is ¥21,409
¥44,972 total
includes taxes & fees
Jun 16 - Jun 17
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

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 ¥28,418
¥51,553 total
includes taxes & fees
Jun 9 - Jun 10
Morocco Loft 2BR overlooking city walking mall

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 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 ¥15,007
¥33,320 total
includes taxes & fees
Jun 15 - Jun 16
The Queen of Winchester Three Bedroom with Upper Level Deck

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
6.0 out of 10, (1 review)
The price is ¥17,562
¥31,836 total
includes taxes & fees
Jun 21 - Jun 22
The Stock Exchange downtown 3rd floor studio apt

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 ¥18,360
¥30,750 total
includes taxes & fees
Jun 30 - Jul 1
The Blue Door steps from Handley Library

"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, (2 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 ¥34,644
¥41,113 total
includes taxes & fees
Jun 4 - Jun 5
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

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 ¥39,028
¥67,053 total
includes taxes & fees
Jul 3 - Jul 4
Scarborough Fair walk to downtown two story apt

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
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is ¥27,939
¥52,999 total
includes taxes & fees
Jun 9 - Jun 10
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

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
9.4 out of 10, Exceptional, (8 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

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 ¥22,713
¥59,116 total
includes taxes & fees
Jul 1 - Jul 2
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (40 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 ¥16,466
¥18,492 total
includes taxes & fees
Jun 9 - Jun 10
Roadhaven1830

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (44 reviews)
"Everything was great"
United States
Lori Anne
The price is ¥19,397
¥36,901 total
includes taxes & fees
Jun 4 - Jun 5
Cozy 1BR Apt Minutes From Skyline Drive!!

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, (18 reviews)
"A very nice place, very clean. The owners were very responsive and helpful. We would definitely stay here again."
United States
Christine H.
The price is ¥17,210
¥32,458 total
includes taxes & fees
Jun 8 - Jun 9
Loft Apt Just off C&O near Harpers Ferry and AT

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Luray
9.8 out of 10, Exceptional, (18 reviews)
"Cute place as described!"
United States
Heather L.
The price is ¥31,585
¥49,293 total
includes taxes & fees
Jun 4 - Jun 5
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (24 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
The price is ¥18,440
¥32,069 total
includes taxes & fees
Jun 14 - Jun 15
Beautiful, Historic, Hiking, Biking and C&O Canal
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

Find out more about Winchester

Winchester Apartments information

Number of reviews
244
Accommodation
203 Apartments
Lowest Price
¥18,492
Highest Price
¥67,053

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. Private yards and Smart TVs are included. Free parking and a terrace are on site.
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 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.