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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Apartments in Winchester

Pretty Little Apt by the Train II
Interior

Pretty Little Apt by the Train II

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great time. Love this city"
The price is AED 477
AED 803 total
includes taxes & fees
6 Oct - 7 Oct
Pretty Little Apt by the Train II
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
2 bedrooms, travel crib, WiFi, bed sheets

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

The price is AED 364
AED 1,227 total
includes taxes & fees
6 Oct - 7 Oct
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (18)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AED 496
AED 855 total
includes taxes & fees
6 Oct - 7 Oct
Apple Mountain Retreat
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Private kitchen

Cameron Grace Charming loft 1-bedroom apt in downtown Winchester

2.0 star property
The price is AED 569
AED 953 total
includes taxes & fees
6 Oct - 7 Oct
Cameron Grace Charming loft 1-bedroom apt in downtown Winchester
Skyland Hideaway | Mountain Cabin w/ Hot Tub
TV, fireplace, offices

Skyland Hideaway | Mountain Cabin w/ Hot Tub

10.0 out of 10, Exceptional, (14)
"We just stayed at SkyLand The house was clean, comfortable and welcoming. Matt is a great host Very responsive. The hot tub needed more water...no big deal. The beds were comfy and the coffee much appreciated upon arrival. Definitely wanna stay again."
The price is AED 522
AED 1,313 total
includes taxes & fees
22 Oct - 23 Oct
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Private apartment on a beautiful private farm!
Property grounds

Private apartment on a beautiful private farm!

10.0 out of 10, Exceptional, (5)
"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. "
The price is AED 496
AED 1,001 total
includes taxes & fees
6 Oct - 7 Oct
Private apartment on a beautiful private farm!
Cozy English Basement Apt quiet but close to downtown
Exterior

Cozy English Basement Apt quiet but close to downtown

9.6 out of 10, Exceptional, (7)
"Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room."
The price is AED 367
AED 645 total
includes taxes & fees
20 Oct - 21 Oct
Cozy English Basement Apt quiet but close to downtown
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Interior

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

10.0 out of 10, Exceptional, (1)
"Jessica was a wonderful host. Outdoor table was lovely with a great view of a garden with cows as next door neighbors "
The price is AED 446
AED 911 total
includes taxes & fees
14 Oct - 15 Oct
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Rosamond nice downtown studio apt
Interior

Rosamond nice downtown studio apt

8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
The price is AED 404
AED 707 total
includes taxes & fees
6 Oct - 7 Oct
Rosamond nice downtown studio apt
Morocco Loft 2BR overlooking city walking mall
Living area

Morocco Loft 2BR overlooking city walking mall

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property with all the comforts of home"
The price is AED 654
AED 1,169 total
includes taxes & fees
21 Oct - 22 Oct
Morocco Loft 2BR overlooking city walking mall
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Private kitchen

Cozy studio close to Skyline Drive, Hiking, and Main Street.

9.0 out of 10, Wonderful, (2)
"Spent the day in the park , very convenient "
The price is AED 624
AED 789 total
includes taxes & fees
12 Oct - 13 Oct
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Microwave, oven, stovetop, dishwasher

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

The price is AED 808
AED 1,427 total
includes taxes & fees
6 Oct - 7 Oct
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
The Blue Door steps from Handley Library
Exterior detail

The Blue Door steps from Handley Library

2.0 star property
7.0 out of 10, Good, (2)
"Perfect. Met all expectations. Small but Great."
The price is AED 422
AED 707 total
includes taxes & fees
4 Nov - 5 Nov
The Blue Door steps from Handley Library
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Dining

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

9.0 out of 10, Wonderful, (6)
"Our Wonder Clock stay was great. Everything was as expected. Location to downtown was awesome and very easily walkable. Our stay was cut short unexpectedly, but we would stay here again! The host was very responsive to one concern we had and was willing to fix immediately. "
The price is AED 753
AED 1,382 total
includes taxes & fees
6 Oct - 7 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Scarborough Fair walk to downtown two story apt
Terrace/patio

Scarborough Fair walk to downtown two story apt

9.6 out of 10, Exceptional, (4)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
The price is AED 815
AED 1,436 total
includes taxes & fees
6 Oct - 7 Oct
Scarborough Fair walk to downtown two story apt
Nostalgia Lane in the heart of the city
3 bedrooms, iron/ironing board, WiFi, bed sheets

Nostalgia Lane in the heart of the city

8.8 out of 10, Excellent, (13)
"Great location in the heart of Winchester. Walking distance to everything. "
The price is AED 680
AED 1,203 total
includes taxes & fees
15 Oct - 16 Oct
Nostalgia Lane in the heart of the city
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Exterior

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

10.0 out of 10, Exceptional, (5)
"Our stay was positively excellent. The property was extremely well-kept and clean. The king bed was so comfortable, and the master bedroom was magical. The hot tub was the icing on the cake, and the views were stunning. I would recommend this property to anyone looking to get away from the hustle and bustle of every day living."
The price is AED 628
AED 1,572 total
includes taxes & fees
15 Oct - 16 Oct
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
The Honeymoon Cabin | Private Retreat w/ hot tub
Outdoor spa tub

The Honeymoon Cabin | Private Retreat w/ hot tub

The price is AED 477
AED 1,329 total
includes taxes & fees
7 Oct - 8 Oct
The Honeymoon Cabin | Private Retreat w/ hot tub
Road Haven 1830
Garden

Road Haven 1830

3.0 star property
9.6 out of 10, Exceptional, (36)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is AED 474
AED 532 total
includes taxes & fees
7 Oct - 8 Oct
Road Haven 1830
Loft Apt Just off C&O near Harpers Ferry, AT, train to DC, & Frederick
Fridge, microwave, oven, stovetop

Loft Apt Just off C&O near Harpers Ferry, AT, train to DC, & Frederick

10.0 out of 10, Exceptional, (15)
"Everything is as it seemed. Very nice accomodations, the extras go above. We will stay again if we are in the area. "
The price is AED 324
AED 674 total
includes taxes & fees
6 Oct - 7 Oct
Loft Apt Just off C&O near Harpers Ferry, AT, train to DC, & Frederick
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"The staff was very nice and the property was clean. I was a little surprised there was no carpeting, no pull out sofa and no microwave in the room. Also the pool water was extremely cold and there was no closet in the room."
Joanne 1-night trip
Posted 20 hours ago
TRU By Hilton Winchester

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 27 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: Road Haven 1830: 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 27 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 Winchester Little Theater, 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.