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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 HK$1,058
HK$1,832 total
includes taxes & fees
25 May - 26 May
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 HK$1,058
HK$2,099 total
includes taxes & fees
25 May - 26 May
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 HK$1,450
HK$2,574 total
includes taxes & fees
25 May - 26 May
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 HK$784
HK$1,376 total
includes taxes & fees
25 May - 26 May
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 HK$737
HK$1,626 total
includes taxes & fees
26 May - 27 May
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 HK$952
HK$2,059 total
includes taxes & fees
27 May - 28 May
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 HK$1,255
HK$2,363 total
includes taxes & fees
25 May - 26 May
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 HK$862
HK$1,562 total
includes taxes & fees
25 May - 26 May
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 HK$1,081
HK$1,838 total
includes taxes & fees
25 May - 26 May
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 HK$1,606
HK$2,814 total
includes taxes & fees
25 May - 26 May
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 HK$705
HK$2,430 total
includes taxes & fees
25 May - 26 May
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 HK$1,739
HK$3,116 total
includes taxes & fees
25 May - 26 May
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 HK$1,528
HK$2,814 total
includes taxes & fees
26 May - 27 May
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)
The price is HK$1,144
HK$2,015 total
includes taxes & fees
26 May - 27 May
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 HK$1,700
HK$2,009 total
includes taxes & fees
25 May - 26 May
"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 HK$1,058
HK$1,188 total
includes taxes & fees
25 May - 26 May
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 HK$776
HK$1,404 total
includes taxes & fees
25 May - 26 May
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 HK$1,034
HK$1,935 total
includes taxes & fees
25 May - 26 May
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 HK$1,049
HK$2,054 total
includes taxes & fees
26 May - 27 May
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 HK$952
HK$1,828 total
includes taxes & fees
29 May - 30 May
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
HK$1,188
Highest Price
HK$3,116

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 27 apartments in Winchester for your trip. Take time to enjoy the array of shops and top-notch restaurants in this vibrant area.
Why should you consider an apartment versus a traditional hotel?
Often more spacious than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for solo travellers who want to stay in a quieter area.
What's the best apartment for my stay in Winchester?
Here is a favourite apartment in the area: Roadhaven1830: Located in Mount Jackson , 39.9 mi/64.2 km away. Includes a private garden and a Smart TV . Free parking and a terrace are on site .
How many apartments are there in Winchester?
Expedia has 27 apartments to book in Winchester.
What will the weather be like when I travel to Winchester?
Although 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 temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What should I see in Winchester?
Travellers 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 make your trip smoother 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 International Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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