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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Winchester apartments

Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is CA $178
CA $299 total
includes taxes & fees
Apr 26 - Apr 27
Pretty Little Apt by the Train II
Property grounds

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 $184
CA $371 total
includes taxes & fees
Apr 27 - Apr 28
Lunar Loft, with mountain views
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (23 reviews)
"Great place to stayed "
United States
Mike F.
The price is CA $184
CA $316 total
includes taxes & fees
Apr 27 - Apr 28
Apple Mountain Retreat
Smart TV

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 $253
CA $458 total
includes taxes & fees
Apr 26 - Apr 27
Nostalgia Lane in the heart of the city
Living area

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 $243
CA $446 total
includes taxes & fees
Apr 27 - Apr 28
Morocco Loft 2BR overlooking city walking mall
Interior

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is CA $150
CA $263 total
includes taxes & fees
Apr 26 - Apr 27
Rosamond nice downtown studio apt
Fridge, microwave, oven, stovetop

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 $129
CA $284 total
includes taxes & fees
Apr 26 - Apr 27
The Queen of Winchester Three Bedroom with Upper Level Deck
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
The price is CA $96
CA $209 total
includes taxes & fees
Apr 26 - Apr 27
Very charming & spacious 2 bedrm
Terrace/patio

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, (7 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 $137
CA $240 total
includes taxes & fees
May 24 - May 25
Cozy English Basement Apt quiet but close to downtown
Property grounds

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
9.8 out of 10, Exceptional, (10 reviews)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is CA $172
CA $357 total
includes taxes & fees
May 5 - May 6
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Smart TV, books

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
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is CA $189
CA $322 total
includes taxes & fees
May 12 - May 13
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Dining

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 $280
CA $511 total
includes taxes & fees
Apr 26 - Apr 27
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Smart TV, fireplace

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, (6 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 $303
CA $542 total
includes taxes & fees
Apr 26 - Apr 27
Scarborough Fair walk to downtown two story apt
Exterior detail

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 $150
CA $273 total
includes taxes & fees
May 4 - May 5
The Stock Exchange downtown 3rd floor studio apt
Interior

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 $123
CA $393 total
includes taxes & fees
Apr 28 - Apr 29
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Smart TV

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 $200
CA $355 total
includes taxes & fees
Apr 29 - Apr 30
Yellow Submarine trendy basement apt and courtyard
Interior

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, (4 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is CA $301
CA $537 total
includes taxes & fees
Apr 24 - Apr 25
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Property grounds

"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 $296
CA $353 total
includes taxes & fees
May 11 - May 12
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Double Room, Ensuite | Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
The price is CA $177
CA $199 total
includes taxes & fees
May 4 - May 5
Roadhaven1830
Outdoor dining

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
9.8 out of 10, Exceptional, (64 reviews)
"The apartment was extremely nice. Everything that was needed for a great stay. I would definitely stay there again."
United States
Tommy N.
The price is CA $226
CA $345 total
includes taxes & fees
Apr 24 - Apr 25
Historic 2-Bedroom in Old Town Warrenton, Virginia
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

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent
" Breakfast was really good, great selection. Parking was plentiful and spacious. "
NEIL 2-night trip
Posted 5 hours ago
Quality Inn Harpers Ferry - Charles Town

Find out more about Winchester

Winchester Apartments information

Number of reviews
206
Accommodation
184 Apartments
Lowest Price
CA $199
Highest Price
CA $542

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?
Here is a top apartment in the area: Roadhaven1830: 39.9 mi/64.2 km away in Mount Jackson.
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.

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