Apartments in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured 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 NZ$364
includes taxes & fees
18 Sept - 19 Sept
Pretty Little Apt by the Train II
Private apartment on a beautiful private farm!
Property grounds

Private apartment on a beautiful private farm!

10.0 out of 10, Exceptional, (4)
"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 NZ$472
includes taxes & fees
1 Sept - 2 Sept
Private apartment on a beautiful private farm!
The Stock Exchange downtown 3rd floor studio apt
Fridge, microwave, oven, stovetop

The Stock Exchange downtown 3rd floor studio apt

2.0 star property
6.0 out of 10, (1)
The Stock Exchange downtown 3rd floor studio apt
Berryville Bliss: Basement Apartment in welcoming Berryville
Outdoor dining

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (3)
"Clean, comfortable and close to Historic Rosemont! Pool was incredible!"
The price is NZ$772
includes taxes & fees
26 Aug - 27 Aug
Berryville Bliss: Basement Apartment in welcoming Berryville
Rosamond nice downtown studio apt
Interior

Rosamond nice downtown studio apt

8.0 out of 10, Very good, (2)
"Small but appropriately priced."
Rosamond nice downtown studio apt
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Private kitchen

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 NZ$452
includes taxes & fees
8 Sept - 9 Sept
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
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 Blue Door steps from Handley Library
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, (10)
"Great location in the heart of Winchester. Walking distance to everything. "
The price is NZ$561
includes taxes & fees
19 Aug - 20 Aug
Nostalgia Lane in the heart of the city
Scarborough Fair walk to downtown two story apt
Terrace/patio

Scarborough Fair walk to downtown two story apt

9.4 out of 10, Exceptional, (3)
"We stayed here overnight after our trip to Shenandoah. House had everything we needed for a peaceful night. "
The price is NZ$668
includes taxes & fees
26 Aug - 27 Aug
Scarborough Fair walk to downtown two story apt
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Fridge, microwave, oven, stovetop

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

2.0 star property
8.0 out of 10, Very good, (3)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
The price is NZ$392
includes taxes & fees
19 Aug - 20 Aug
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Apple Mountain Retreat
Property grounds

Apple Mountain Retreat

10.0 out of 10, Exceptional, (14)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is NZ$395
includes taxes & fees
20 Aug - 21 Aug
Apple Mountain Retreat
Balcony & Pool Access: Modern Gainesville Home
Apartment (4 Bedrooms) | Interior

Balcony & Pool Access: Modern Gainesville Home

3.5 star property
The price is NZ$746
includes taxes & fees
19 Aug - 20 Aug
Balcony & Pool Access: Modern Gainesville Home
Beautiful: Historic, Hiking, Biking and C&O Canal near Harpers Ferry & Frederick
Exterior

Beautiful: Historic, Hiking, Biking and C&O Canal near Harpers Ferry & Frederick

10.0 out of 10, Exceptional, (15)
"Absolutely loved staying in this historic apartment! The hosts are incredibly friendly and the area is very walkable with local food and shops within a quarter to half mile. Such a great experience here, can’t recommend it enough and can’t wait to stay again!"
The price is NZ$270
includes taxes & fees
22 Aug - 23 Aug
Beautiful: Historic, Hiking, Biking and C&O Canal near Harpers Ferry & Frederick
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, (14)
"Very nice stay!"
The price is NZ$314
includes taxes & fees
24 Aug - 25 Aug
Loft Apt Just off C&O near Harpers Ferry, AT, train to DC, & Frederick
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC
Fridge, microwave, oven, stovetop

Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

9.8 out of 10, Exceptional, (41)
"This location was perfect for a weekend visit to the area for getting on the C&O and exploring local hikes and wineries!"
The price is NZ$270
includes taxes & fees
19 Aug - 20 Aug
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Desk, iron/ironing board, free WiFi, bed sheets

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

9.8 out of 10, Exceptional, (17)
"Cute farm, nice family. Place as advertised. Close to beautiful country and lots of vineyards."
The price is NZ$462
includes taxes & fees
19 Aug - 20 Aug
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Historic apartment in Old Town Warrenton, Virginia
Outdoor dining

Historic apartment in Old Town Warrenton, Virginia

9.8 out of 10, Exceptional, (48)
"The property was top notch! It was as comfortable as any 5 star hotels we have stayed in. Upon arrival we took advantage of the outdoor dining area and had drinks before leaving for dinner. The linens were also soft and fluffy. The rooms were beautifully decorated."
The price is NZ$393
includes taxes & fees
19 Aug - 20 Aug
Historic apartment in Old Town Warrenton, Virginia
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Interior

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

10.0 out of 10, Exceptional, (3)
"Clean, cute, hot water, cool inside. I would stay again!!!"
The price is NZ$448
includes taxes & fees
25 Aug - 26 Aug
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Best location! The Pullman Apt @ historic 1799 Inn
Dining

Best location! The Pullman Apt @ historic 1799 Inn

9.4 out of 10, Exceptional, (38)
"We had a great stay. The location is superb. It was a perfect getaway. The host was very communicative and the place was very nice. "
The price is NZ$409
includes taxes & fees
18 Sept - 19 Sept
Best location! The Pullman Apt @ historic 1799 Inn
Best location! The Iron Horse @ historic 1799 Inn
Property grounds

Best location! The Iron Horse @ historic 1799 Inn

9.6 out of 10, Exceptional, (8)
"Perfect location, very nice accommodations! Loved the layout of the top apartment and loved the close proximity to many restaurants and trails. Would love to come back!"
The price is NZ$505
includes taxes & fees
18 Sept - 19 Sept
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.
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 Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent
"Girls trip with 3 of us. I travel a lot and I was very impressed with the cleanliness and friendliness of this hotel. "
Marilyn 1-night trip
Posted 1 day ago
Hampton Inn Winchester N/Conference Center, VA

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 24 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?
Here is a favourite apartment in the area: Family Farmhouse Inn: It's located in Mount Jackson , 39.9 mi/64.2 km away.
How many apartments are there in Winchester?
Expedia has 24 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 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 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.