Apartments in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Winchester apartments

Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (23 reviews)
"Great place to stayed "
United States
Mike F.
The price is NZ$390
includes taxes & fees
27 Apr - 28 Apr
Apple Mountain Retreat
Property grounds

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (8 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 NZ$457
includes taxes & fees
21 Apr - 22 Apr
Lunar Loft, with mountain views
Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is NZ$370
includes taxes & fees
21 Apr - 22 Apr
Pretty Little Apt by the Train II
Property grounds

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

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
9.8 out of 10, Exceptional, (10 reviews)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is NZ$443
includes taxes & fees
4 May - 5 May
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to 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, (16 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is NZ$557
includes taxes & fees
21 Apr - 22 Apr
Nostalgia Lane in the heart of the city
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is NZ$547
includes taxes & fees
21 Apr - 22 Apr
Morocco Loft 2BR overlooking city walking mall
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.
Rosamond nice downtown studio apt
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
The price is NZ$259
includes taxes & fees
26 Apr - 27 Apr
Very charming & spacious 2 bedrm
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
9.2 out of 10, Wonderful, (7 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is NZ$620
includes taxes & fees
21 Apr - 22 Apr
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
Old Town Winchester
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
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The Queen of Winchester Three Bedroom with Upper Level Deck
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
Winchester Historic District
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is NZ$401
includes taxes & fees
21 Apr - 22 Apr
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
6.0 out of 10, (1 review)
The price is NZ$337
includes taxes & fees
3 May - 4 May
The Stock Exchange downtown 3rd floor studio apt
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 NZ$480
includes taxes & fees
22 Apr - 23 Apr
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
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, (4 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

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)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
The price is NZ$431
includes taxes & fees
29 Apr - 30 Apr
Yellow Submarine trendy basement apt and courtyard
Outdoor dining

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (1 review)
"Kay and Joe are wonderful guests. They went above and beyond to made us feel so welcomed. The Love Nest is the most cozy and wonderful place we stayed in. Their property is gorgeous and very peaceful. Everything we needed to unwind from a hard week. We will be coming back soon!"
United States
Mariana F.
The price is NZ$432
includes taxes & fees
4 May - 5 May
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Double Room, Ensuite | Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (40 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 NZ$258
includes taxes & fees
22 Apr - 23 Apr
Roadhaven1830
Exterior detail

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (57 reviews)
"Host was welcoming and place was as described and in very clean condition. "
United States
Junaid B.
The price is NZ$305
includes taxes & fees
21 Apr - 22 Apr
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Outdoor dining

Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
9.8 out of 10, Exceptional, (64 reviews)
"The apartment was extremely nice. Everything that was needed for a great stay. I would definitely stay there again."
United States
Tommy N.
The price is NZ$425
includes taxes & fees
21 Apr - 22 Apr
Historic 2-Bedroom in Old Town Warrenton, Virginia
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.
View all properties
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

Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA

10/10 Excellent
"It’s probably the cleanest Red Roof Hotel I’ve ever been to and what made it difference is they’re all inside rooms so you feel safe and secure The staff and the people we met were all very nice and we will stay there again next year when we come down for the Leesburg flower and garden festival"
David 3-night trip
Posted 1 hour ago
Red Roof Inn Leesburg, VA

Find out more about Winchester

Winchester Apartments information

Number of reviews
263
Accommodation
168 Apartments
Lowest Price
NZ$258
Highest Price
NZ$620

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 26 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's a top apartment in the area: Roadhaven1830: 39.9 mi/64.2 km away in Mount Jackson .
How many apartments are there in Winchester?
Expedia has 26 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 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 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.