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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 CA $187
CA $320 total
includes taxes & fees
May 26 - May 27
Apple Mountain Retreat

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (8 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 CA $187
CA $376 total
includes taxes & fees
May 26 - May 27
Lunar Loft, with mountain views

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 CA $256
CA $465 total
includes taxes & fees
May 26 - May 27
Nostalgia Lane in the heart of the city

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, (8 reviews)
"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 traveller
The price is CA $138
CA $243 total
includes taxes & fees
May 31 - Jun 1
Cozy English Basement Apt quiet but close to downtown

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 CA $130
CA $290 total
includes taxes & fees
May 26 - May 27
The Queen of Winchester Three Bedroom with Upper Level Deck

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)
"The location was perfect for my needs, the apartment was super cute - a charming older home with modern upgrades and a designer feel. The host was very communicative and welcoming, so I had all the information I needed and knew just what to expect. I hope I get a chance to stay there again! "
United States
Ren
The price is CA $168
CA $371 total
includes taxes & fees
May 27 - May 28
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 CA $221
CA $421 total
includes taxes & fees
May 26 - May 27
Morocco Loft 2BR overlooking city walking mall

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 CA $152
CA $277 total
includes taxes & fees
May 26 - May 27
The Stock Exchange downtown 3rd floor studio apt

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 CA $191
CA $326 total
includes taxes & fees
May 26 - May 27
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

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
9.2 out of 10, Wonderful, (7 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is CA $283
CA $520 total
includes taxes & fees
May 26 - May 27
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 CA $124
CA $433 total
includes taxes & fees
May 26 - May 27
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

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 CA $307
CA $550 total
includes taxes & fees
May 26 - May 27
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 CA $269
CA $501 total
includes taxes & fees
May 26 - May 27
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is CA $202
CA $360 total
includes taxes & fees
May 26 - May 27
Yellow Submarine trendy basement apt and courtyard

"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, (1 review)
"Kay and Joe are wonderful guests. They went above and beyond to made us feel so welcomed. The Love Nest is the most cozy and wonderful place we stayed in. Their property is gorgeous and very peaceful. Everything we needed to unwind from a hard week. We will be coming back soon!"
United States
Mariana F.
The price is CA $300
CA $357 total
includes taxes & fees
May 26 - May 27
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

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 CA $181
CA $203 total
includes taxes & fees
May 26 - May 27
Roadhaven1830

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (60 reviews)
"Host was welcoming and place was as described and in very clean condition. "
United States
Junaid B.
The price is CA $137
CA $248 total
includes taxes & fees
May 26 - May 27
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (6 reviews)
"Clean, great location, and charming/updated space. Highly recommend! Host was super communicative and helpful!! "
United States
Kaitlin L.
The price is CA $182
CA $346 total
includes taxes & fees
May 26 - May 27
Historic Getaway near C&O Canal, hiking and biking

The Little Red Schoolhouse

The Little Red Schoolhouse
Cross Junction
9.8 out of 10, Exceptional, (14 reviews)
"Lovely two night stay. The hot tub was clean and enjoyable as quick get away for my husband and me. Would absolutely stay again and refer others to do the same. "
United States
Nikki B.
The price is CA $201
CA $389 total
includes taxes & fees
May 31 - Jun 1
The Little Red Schoolhouse

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (44 reviews)
"Love that my pet was welcome. Very quiet location and felt like home. "
United States
Theresa S.
The price is CA $168
CA $324 total
includes taxes & fees
May 26 - May 27
Cozy 1BR Apt Minutes From Skyline Drive!!
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
196
Accommodation
184 Apartments
Lowest Price
CA $203
Highest Price
CA $550

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's a top apartment in the area: Roadhaven1830: Located in Mount Jackson, 39.9 mi/64.2 km away. Includes private yards and Smart TVs. Free parking and a terrace are on site.
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.

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