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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Winchester apartments

Interior
Rosamond nice downtown studio apt

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
United States
John M.
The price is AED 404
AED 707 total
includes taxes & fees
29 Jan - 30 Jan
Rosamond nice downtown studio apt
Property grounds
Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!

Private apartment on a beautiful private farm!
Bluemont
8.8 out of 10, Excellent, (6)
"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 AED 496
AED 992 total
includes taxes & fees
12 Jan - 13 Jan
Private apartment on a beautiful private farm!
Property grounds
Apple Mountain Retreat

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (21)
"Great place to stayed "
United States
Mike F.
The price is AED 496
AED 855 total
includes taxes & fees
9 Jan - 10 Jan
Apple Mountain Retreat
Interior
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very Good, (1)
"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 AED 419
AED 1,129 total
includes taxes & fees
3 Feb - 4 Feb
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Exterior detail
The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
Winchester Historic District
6.0 out of 10, (1)
The price is AED 404
AED 728 total
includes taxes & fees
29 Jan - 30 Jan
The Stock Exchange downtown 3rd floor studio apt
Smart TV
Nostalgia Lane in the heart of the city

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, (14)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is AED 680
AED 1,165 total
includes taxes & fees
11 Jan - 12 Jan
Nostalgia Lane in the heart of the city
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

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
Winchester Historic District
8.6 out of 10, Excellent, (4)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
The price is AED 507
AED 845 total
includes taxes & fees
18 Jan - 19 Jan
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV
Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
The price is AED 536
AED 928 total
includes taxes & fees
1 Feb - 2 Feb
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

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (1)
"Beautiful space; helpful host."
United States
Sally C.
The price is AED 808
AED 1,432 total
includes taxes & fees
11 Jan - 12 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

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
9.0 out of 10, Wonderful, (6)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is AED 753
AED 1,303 total
includes taxes & fees
11 Jan - 12 Jan
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

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (5)
"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 AED 815
AED 1,440 total
includes taxes & fees
12 Jan - 13 Jan
Scarborough Fair walk to downtown two story apt
Garden
Roadhaven1830

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (38)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
United States
Carri
The price is AED 496
AED 557 total
includes taxes & fees
9 Jan - 10 Jan
Roadhaven1830
Beach
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
2.0 star property
Berkeley Springs
10.0 out of 10, Exceptional, (1)
"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.
The price is AED 308
AED 662 total
includes taxes & fees
9 Jan - 10 Jan
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Outdoor spa tub
Luray Downtown / Hot Tub / Game Room / Firepit

Luray Downtown / Hot Tub / Game Room / Firepit

Luray Downtown / Hot Tub / Game Room / Firepit
Luray
9.8 out of 10, Exceptional, (7)
"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.
The price is AED 410
AED 1,116 total
includes taxes & fees
9 Jan - 10 Jan
Luray Downtown / Hot Tub / Game Room / Firepit
Terrace/patio
Elegant Retreat w/Vintage Charm & Modern Comforts

Elegant Retreat w/Vintage Charm & Modern Comforts

Elegant Retreat w/Vintage Charm & Modern Comforts
Luray
9.8 out of 10, Exceptional, (6)
"Quaint house in a small town with a wonderdul trail right behind the residence."
United States
Amber K.
The price is AED 288
AED 488 total
includes taxes & fees
11 Jan - 12 Jan
Elegant Retreat w/Vintage Charm & Modern Comforts
Exterior
Downtown Loft by Brewery & Trails

Downtown Loft by Brewery & Trails

Downtown Loft by Brewery & Trails
2.0 star property
Brunswick
The price is AED 294
AED 846 total
includes taxes & fees
2 Feb - 3 Feb
Downtown Loft by Brewery & Trails
Interior
Loft Apt Just off C&O near Harpers Ferry and AT

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, (16)
"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 AED 360
AED 677 total
includes taxes & fees
12 Jan - 13 Jan
Loft Apt Just off C&O near Harpers Ferry and AT
Interior
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Warrenton
10.0 out of 10, Exceptional, (4)
"I love staying here! It's cozy and comfortable and in a perfect location. "
United States
Jenny D.
The price is AED 606
AED 976 total
includes taxes & fees
15 Jan - 16 Jan
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Exterior
The San Francisco Way

The San Francisco Way

The San Francisco Way
Martinsburg
9.4 out of 10, Exceptional, (3)
"Super cute, great spot, affordable. Would stay again if I visit Martinsburg. "
United States
Alex R.
The price is AED 309
AED 682 total
includes taxes & fees
13 Jan - 14 Jan
The San Francisco Way
Exterior
Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
10.0 out of 10, Exceptional, (1)
"Clean, great location, and charming/updated space. Highly recommend! Host was super communicative and helpful!! "
United States
Kaitlin L.
The price is AED 441
AED 864 total
includes taxes & fees
12 Jan - 13 Jan
Historic Getaway near C&O Canal, hiking and biking
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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Yes"
Ken 1-night trip
Posted 1 day ago
Hampton Inn Martinsburg

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 favorite apartment in the area: Roadhaven1830: Situated in Mount Jackson, 39.9 mi/64.2 km from the heart of Winchester.
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.