Search Apartments in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Winchester apartments

Interior
Rosamond nice downtown studio apt

Apartment in Winchester Historic District

Rosamond nice downtown studio apt
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is €169
includes taxes & fees
29 Jan - 30 Jan
Rosamond nice downtown studio apt
Property grounds
Private apartment on a beautiful private farm!

Apartment in Bluemont

Private apartment on a beautiful private farm!
8.8 out of 10, Excellent, (6 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 €237
includes taxes & fees
27 Jan - 28 Jan
Private apartment on a beautiful private farm!
Property grounds
Apple Mountain Retreat

Apartment in Linden

Apple Mountain Retreat
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stayed "
United States
Mike F.
The price is €202
includes taxes & fees
15 Jan - 16 Jan
Apple Mountain Retreat
Exterior detail
The Stock Exchange downtown 3rd floor studio apt

Apartment in Winchester Historic District

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
6.0 out of 10, (1 review)
The Stock Exchange downtown 3rd floor studio apt
Interior
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Apartment in Fauquier County

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
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 €258
includes taxes & fees
9 Feb - 10 Feb
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Smart TV
Nostalgia Lane in the heart of the city

Apartment in Old Town Winchester

Nostalgia Lane in the heart of the city
9.0 out of 10, Wonderful, (14 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
Nostalgia Lane in the heart of the city
Smart TV, books
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Apartment in Winchester Historic District

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
8.6 out of 10, Excellent, (4 reviews)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
The price is €206
includes taxes & fees
21 Jan - 22 Jan
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV
Yellow Submarine trendy basement apt and courtyard

Apartment in Old Town Winchester

Yellow Submarine trendy basement apt and courtyard
7.6 out of 10, Good, (4 reviews)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
Yellow Submarine trendy basement apt and courtyard
Interior
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Apartment in Old Town Winchester

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
10.0 out of 10, Exceptional, (1 review)
"Beautiful space; helpful host."
United States
Sally C.
The price is €342
includes taxes & fees
18 Jan - 19 Jan
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Dining
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

Apartment in Old Town Winchester

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
9.0 out of 10, Wonderful, (6 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
Smart TV, fireplace
Scarborough Fair walk to downtown two story apt

Apartment in Old Town Winchester

Scarborough Fair walk to downtown two story apt
9.6 out of 10, Exceptional, (5 reviews)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
The price is €344
includes taxes & fees
15 Jan - 16 Jan
Scarborough Fair walk to downtown two story apt
Garden
Roadhaven1830

Apartment in Mount Jackson

Roadhaven1830
3.0 star property
9.6 out of 10, Exceptional, (38 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 €130
includes taxes & fees
15 Jan - 16 Jan
Roadhaven1830
Beach
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Apartment in Berkeley Springs

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Everything from booking the stay to arriving and checking in was quick and convenient. The host emailed us directions and was easy to navigate toThe owl was just the perfect size for "
United States
kayla c.
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Terrace/patio
Vintage Elegance w/Floral Accents & Timeless Decor

Apartment in Luray

Vintage Elegance w/Floral Accents & Timeless Decor
The price is €148
includes taxes & fees
28 Jan - 29 Jan
Vintage Elegance w/Floral Accents & Timeless Decor
Exterior
Downtown Loft by Brewery & Trails

Apartment in Brunswick

Downtown Loft by Brewery & Trails
2.0 star property
The price is €182
includes taxes & fees
20 Jan - 21 Jan
Downtown Loft by Brewery & Trails
2 bedrooms, iron/ironing board, WiFi, bed sheets
Tiny Cabin w Fire Pit Game Room and Dog Friendly

Apartment in Great Cacapon

Tiny Cabin w Fire Pit Game Room and Dog Friendly
10.0 out of 10, Exceptional, (3 reviews)
"Lovely little cabin, everything we needed for a short weekend stay. Very cozy and comfortable. "
United States
Abigail G.
The price is €231
includes taxes & fees
15 Jan - 16 Jan
Tiny Cabin w Fire Pit Game Room and Dog Friendly
Interior
Loft Apt Just off C&O near Harpers Ferry and AT

Apartment in Brunswick

Loft Apt Just off C&O near Harpers Ferry and AT
10.0 out of 10, Exceptional, (16 reviews)
"Our Hosts were wonderful and the space was great. It sits right off of the bike trail and across the street from a great bakery and bike shop. We thoroughly enjoyed our stay."
United States
Mark B.
The price is €161
includes taxes & fees
16 Jan - 17 Jan
Loft Apt Just off C&O near Harpers Ferry and AT
Fridge, microwave, oven, stovetop
The Little Red Schoolhouse

Apartment in Cross Junction

The Little Red Schoolhouse
9.8 out of 10, Exceptional, (13 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 Little Red Schoolhouse
Outdoor spa tub
Luray Downtown / Hot Tub / Game Room / Firepit

Apartment in Luray

Luray Downtown / Hot Tub / Game Room / Firepit
9.8 out of 10, Exceptional, (7 reviews)
"A nice house and great amenities. We enjoyed our stay and had easy drives to different activities. Perfect for a family short vacation."
United States
Mohamed S.
Luray Downtown / Hot Tub / Game Room / Firepit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Great value for the money."
Michael 1-night trip
Posted 5 days ago
Hampton Inn Martinsburg

Find out more about Winchester

Winchester Apartments information

Number of reviews
135
Accommodation
200 Apartments
Lowest Price
€130
Highest Price
€344

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 26 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?
Below you'll find a favourite apartment in the area: Roadhaven1830: Situated in Mount Jackson , 39.9 mi/64.2 km from the heart of Winchester.
How many apartments are there in Winchester?
Expedia has 26 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.