A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Our top choices for Winchester apartments

1. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
8.8 out of 10, Excellent, (10 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is £133
includes taxes & fees
18 Aug - 19 Aug
Cozy English Basement Apt quiet but close to downtown

2. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 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 price is £203
includes taxes & fees
19 Aug - 20 Aug
The Queen of Winchester Three Bedroom with Upper Level Deck

3. 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 £145
includes taxes & fees
25 Aug - 26 Aug
Rosamond nice downtown studio apt

4. 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
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is £177
includes taxes & fees
31 Aug - 1 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

5. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is £194
includes taxes & fees
18 Aug - 19 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

6. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"It was decorated very cute and the bed was comfortable. Very close to shops and restaurants.We had to drive around the block and get out to find the location because you park and enter through the back door.It’s very close to the train stain but was only interrupted by an early morning train once."
United States
Brenda H.
The price is £164
includes taxes & fees
30 Aug - 31 Aug
Pretty Little Apt by the Train II

7. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is £149
includes taxes & fees
25 Aug - 26 Aug
The Stock Exchange downtown 3rd floor studio apt

8. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is £242
includes taxes & fees
19 Aug - 20 Aug
Nostalgia Lane in the heart of the city

9. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is £184
includes taxes & fees
31 Aug - 1 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

10. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is £239
includes taxes & fees
31 Aug - 1 Sept
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

11. 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, (10 reviews)
"Great location…"
United States
John P.
The price is £276
includes taxes & fees
18 Aug - 19 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

12. 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 £191
includes taxes & fees
16 Sept - 17 Sept
Yellow Submarine trendy basement apt and courtyard

13. 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, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is £291
includes taxes & fees
23 Aug - 24 Aug
Scarborough Fair walk to downtown two story apt

14. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 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 £203
includes taxes & fees
19 Aug - 20 Aug
Lunar Loft, with mountain views

15. "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, (4 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is £196
includes taxes & fees
18 Aug - 19 Aug
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

16. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
The price is £256
includes taxes & fees
7 Sept - 8 Sept
NEW! Historic Schoolhouse HotTub+FirePit+Wineries

17. 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
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
"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 £138
includes taxes & fees
18 Aug - 19 Aug
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

18. Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath

Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Augusta
7.4 out of 10, Good, (3 reviews)
"Great Experience!"
United States
Kimberly B.
The price is £216
includes taxes & fees
18 Aug - 19 Aug
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath

19. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (49 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
The price is £120
includes taxes & fees
18 Aug - 19 Aug
Roadhaven1830

20. Glamping dome w/ hot tub & mountain views

Glamping dome w/ hot tub & mountain views
Augusta
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful stay!"
United States
Eli W.
The price is £229
includes taxes & fees
25 Aug - 26 Aug
Glamping dome w/ hot tub & mountain views
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

Find out more about Winchester

Winchester Apartments information

Number of reviews
49
Accommodation
197 Apartments
Lowest Price
£120
Highest Price
£120

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's a popular apartment in the area: Roadhaven1830: Located 39.9 mi/64.2 km away in Mount Jackson . Free WiFi, a private garden and a Smart TV are included . Free parking and a terrace are on site .
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 Museum of the Shenandoah Valley and Bright Box 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 Stonewall Jackson's Headquarters 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.