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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winchester apartments

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 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!
Bluemont
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 AED 496
AED 992 total
includes taxes & fees
19 Jan - 20 Jan
Private apartment on a beautiful private farm!
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stayed "
United States
Mike F.
The price is AED 496
AED 855 total
includes taxes & fees
16 Jan - 17 Jan
Apple Mountain Retreat
Exterior detail

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 review)
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, books

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 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 AED 507
AED 849 total
includes taxes & fees
21 Jan - 22 Jan
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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 AED 393
AED 1,083 total
includes taxes & fees
9 Feb - 10 Feb
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
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, (14 reviews)
"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
18 Jan - 19 Jan
Nostalgia Lane in the heart of the city
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
Very charming & spacious 2 bedrm
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)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
The price is AED 536
AED 936 total
includes taxes & fees
15 Feb - 16 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
Old Town Winchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful space; helpful host."
United States
Sally C.
The price is AED 808
AED 1,432 total
includes taxes & fees
18 Jan - 19 Jan
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Smart TV, fireplace

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 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 AED 815
AED 1,440 total
includes taxes & fees
18 Jan - 19 Jan
Scarborough Fair walk to downtown two story apt
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
9.0 out of 10, Wonderful, (6 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is AED 753
AED 1,323 total
includes taxes & fees
25 Jan - 26 Jan
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Garden

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
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 AED 496
AED 557 total
includes taxes & fees
16 Jan - 17 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
2.0 star property
Berkeley Springs
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.
The price is AED 308
AED 662 total
includes taxes & fees
16 Jan - 17 Jan
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Terrace/patio

Elegant Retreat w/Vintage Charm & Modern Comforts

Elegant Retreat w/Vintage Charm & Modern Comforts
Luray
9.8 out of 10, Exceptional, (6 reviews)
"Quaint house in a small town with a wonderdul trail right behind the residence."
United States
Amber K.
The price is AED 288
AED 531 total
includes taxes & fees
18 Jan - 19 Jan
Elegant Retreat w/Vintage Charm & Modern Comforts
Interior

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 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 AED 360
AED 674 total
includes taxes & fees
18 Jan - 19 Jan
Loft Apt Just off C&O near Harpers Ferry and AT
Fridge, microwave, oven, stovetop

The Little Red Schoolhouse

The Little Red Schoolhouse
Cross Junction
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 price is AED 234
AED 654 total
includes taxes & fees
21 Jan - 22 Jan
The Little Red Schoolhouse
Exterior

Downtown Loft by Brewery & Trails

Downtown Loft by Brewery & Trails
2.0 star property
Brunswick
The price is AED 606
AED 1,094 total
includes taxes & fees
15 Feb - 16 Feb
Downtown Loft by Brewery & Trails
Terrace/patio

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Luray
9.8 out of 10, Exceptional, (16 reviews)
"It was an amazing place, will recommend to friends and hopefully will be back."
United States
Lucerito I.
The price is AED 546
AED 911 total
includes taxes & fees
19 Jan - 20 Jan
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Iron/ironing board, WiFi, bed sheets

Cozy 1-bedroom studio type living in tranquil Broadlands with AC & private bath.

Cozy 1-bedroom studio type living in tranquil Broadlands with AC & private bath.
2.0 star property
Broadlands
The price is AED 220
AED 544 total
includes taxes & fees
30 Jan - 31 Jan
Cozy 1-bedroom studio type living in tranquil Broadlands with AC & private bath.
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern."
Billy 2-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Winchester

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.