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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Winchester apartments

Smart TV

Apartment in Old Town Winchester

Nostalgia Lane in the heart of the city
9.0 out of 10, Wonderful, (15 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
Property grounds

Apartment in Bluemont

Lunar Loft, with mountain views
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 661
AED 1,214 total
includes taxes & fees
15 Mar - 16 Mar
Lunar Loft, with mountain views
Living area

Apartment in Old Town Winchester

Morocco Loft 2BR overlooking city walking mall
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
Morocco Loft 2BR overlooking city walking mall
Property grounds

Apartment in Bluemont

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
10.0 out of 10, Exceptional, (6 reviews)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Smart TV, books

Apartment in Winchester Historic District

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Interior

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.
Rosamond nice downtown studio apt
Property grounds

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 AED 496
AED 831 total
includes taxes & fees
10 Mar - 11 Mar
Apple Mountain Retreat
Exterior detail

Apartment in Winchester Historic District

The Stock Exchange downtown 3rd floor studio apt
6.0 out of 10, (1 review)
The Stock Exchange downtown 3rd floor studio apt
Dining

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

Apartment in Old Town Winchester

Scarborough Fair walk to downtown two story apt
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.
Scarborough Fair walk to downtown two story apt
Interior

Apartment in Winchester

Very charming & spacious 2 bedrm
Very charming & spacious 2 bedrm
Interior

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 AED 349
AED 1,067 total
includes taxes & fees
5 Mar - 6 Mar
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Interior

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, (2 reviews)
"Beautiful space; helpful host."
United States
Sally C.
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Smart TV

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
Exterior detail

Apartment in Old Town Winchester

The Blue Door steps from Handley Library
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The Blue Door steps from Handley Library
Apartment (3 Bedrooms) | Interior

Apartment in Luray

Charming Townhome < 1 Mi to Zoo & Luray Caverns!
3.5 star property
9.4 out of 10, Exceptional, (9 reviews)
"Enjoyed our stay. The townhouse exceeded our expectations. Well taken care of and convenient the attractions my family were interested in."
United States
Jenifer
The price is AED 540
AED 1,361 total
includes taxes & fees
18 Mar - 19 Mar
Charming Townhome < 1 Mi to Zoo & Luray Caverns!
Garden

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 AED 491
AED 551 total
includes taxes & fees
5 Mar - 6 Mar
Roadhaven1830
Outdoor dining

Apartment in Berkeley Springs

The Downtown Flat at Creekside
10.0 out of 10, Exceptional, (19 reviews)
"Awesome stay. Perfect setting and impeccable place. "
United States
Mark B.
The price is AED 621
AED 1,097 total
includes taxes & fees
11 Mar - 12 Mar
The Downtown Flat at Creekside
1 bedroom, desk, iron/ironing board, free WiFi

Apartment in Purcellville

Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay. The space was very cute and was clean and comfortable. The hosts were helpful and accommodating. We appreciated everything. "
United States
Amanda H.
The price is AED 529
AED 736 total
includes taxes & fees
10 Mar - 11 Mar
Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!
Property grounds

Apartment in Harpers Ferry

Best location! The Iron Horse @ historic 1799 Inn
9.8 out of 10, Exceptional, (11 reviews)
"Lovely inn, we greatly enjoyed our stay!"
United States
Lisa B.
The price is AED 514
AED 950 total
includes taxes & fees
5 Mar - 6 Mar
Best location! The Iron Horse @ historic 1799 Inn
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Yes"
james 1-night trip
Posted 10 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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?
Listed below are some of the more popular apartments in the area: Charming Loft In Winchester Va, Furnished and all Inclusive: Situated in Winchester, 2.9 mi/4.7 km from the heart of Winchester. Historic 2-Bedroom in Old Town Warrenton, Virginia: Located 37.9 mi/61 km away in Warrenton. Free WiFi, private patios, and separate dining areas are included. Access to onsite laundry facilities is available on site. Apple Mountain Retreat: Located in Linden, 18.4 mi/29.6 km away. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. The Downtown Flat at Creekside: 30.8 mi/49.6 km away in Berkeley Springs. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry: It's located in Harpers Ferry, 25 mi/40.2 km from Winchester. Includes free WiFi, fireplaces, and Smart TVs.
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.