Apartments in Winchester

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Winchester apartments

Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stayed "
United States
Mike F.
The price is NZ$391
includes taxes & fees
8 June - 9 June
Apple Mountain Retreat
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
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is NZ$394
includes taxes & fees
21 June - 22 June
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Shower

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (9 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$458
includes taxes & fees
8 June - 9 June
Lunar Loft, with mountain views
TV

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, (1 review)
The price is NZ$488
includes taxes & fees
7 June - 8 June
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
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$563
includes taxes & fees
8 June - 9 June
Nostalgia Lane in the heart of the city
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
10.0 out of 10, Exceptional, (11 reviews)
"Our stay was great, and we had an excellent time in the area. Short drive to hiking spots and within walking distance to the local Bluemont Station restaurant. Highly recommend this stay in a quaint location!"
United States
Nicholas B.
The price is NZ$480
includes taxes & fees
16 June - 17 June
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
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$516
includes taxes & fees
7 June - 8 June
Morocco Loft 2BR overlooking city walking mall
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 price is NZ$350
includes taxes & fees
15 June - 16 June
The Queen of Winchester Three Bedroom with Upper Level Deck
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$338
includes taxes & fees
21 June - 22 June
The Stock Exchange downtown 3rd floor studio apt
Exterior detail

The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is NZ$328
includes taxes & fees
30 June - 1 July
The Blue Door steps from Handley Library
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, (2 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 NZ$437
includes taxes & fees
8 June - 9 June
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
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, (7 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.
The price is NZ$662
includes taxes & fees
15 June - 16 June
Scarborough Fair walk to downtown two story apt
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, (5 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is NZ$563
includes taxes & fees
9 June - 10 June
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
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
9.4 out of 10, Exceptional, (8 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is NZ$625
includes taxes & fees
15 June - 16 June
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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$641
includes taxes & fees
6 July - 7 July
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (40 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back "
United States
Varnell
The price is NZ$199
includes taxes & fees
6 July - 7 July
Roadhaven1830
Smart TV

Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (44 reviews)
"Everything was great"
United States
Lori Anne
The price is NZ$397
includes taxes & fees
6 June - 7 June
Cozy 1BR Apt Minutes From Skyline Drive!!
Interior

Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (18 reviews)
"A very nice place, very clean. The owners were very responsive and helpful. We would definitely stay here again."
United States
Christine H.
The price is NZ$344
includes taxes & fees
7 June - 8 June
Loft Apt Just off C&O near Harpers Ferry and AT
Terrace/patio

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Luray
9.8 out of 10, Exceptional, (18 reviews)
"Cute place as described!"
United States
Heather L.
The price is NZ$488
includes taxes & fees
15 June - 16 June
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Exterior

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (24 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
The price is NZ$340
includes taxes & fees
7 June - 8 June
Beautiful, Historic, Hiking, Biking and C&O Canal
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"The room was clean and very comfortable and parking was on site"
Liliana 1-night trip
Posted 3 hours ago
Spark by Hilton Winchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
244
Accommodation
154 Apartments
Lowest Price
NZ$199
Highest Price
NZ$662

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 popular apartment in the area: Roadhaven1830: Located 39.9 mi/64.2 km away in Mount Jackson . 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 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.