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Apartments in Winchester

Family Farmhouse Inn

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is NT$3,857
NT$4,331 total
includes taxes & fees
Aug 13 - Aug 14
Family Farmhouse Inn

National at Loudoun

3.0 star property
6.8 out of 10, (6)
"Great stay fast communication "
National at Loudoun

Charming Townhome < 1 Mi to Zoo & Luray Caverns!

3.5 star property
9.4 out of 10, Exceptional, (8)
"Enjoyed our stay. The townhouse exceeded our expectations. Well taken care of and convenient the attractions my family were interested in."
Charming Townhome < 1 Mi to Zoo & Luray Caverns!

Front Royal Retreat on 3 Acres w/ Mtn Views!

3.0 star property
Front Royal Retreat on 3 Acres w/ Mtn Views!

Berkeley Springs Haven w/ Sleepy Creek Access!

3.0 star property
7.4 out of 10, Good, (3)
"This little cabin was amazing. The bed was super comfy and the AC unit kept us nice and cool during our stay. The cabin was clean and well stocked on towels and a few other amenities. Will definitely be going back. "
Berkeley Springs Haven w/ Sleepy Creek Access!

Epic Brunswick Apartment With Deck!

3.0 star property
9.0 out of 10, Wonderful, (2)
"Have never stayed at a property with such nice accessories. Kitchen was well-supplied w/ just about everything, incl tea, coffee & even zip lock bags. Portable heater was great. Beds were very comfortable & towels were especially nice. Wifi connectivity was excellent which allowed me to work remotely. They even supplied night lights & flashlights."
Epic Brunswick Apartment With Deck!

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

3.0 star property
10.0 out of 10, Exceptional, (2)
Waterfront Virginia Retreat w/ Canoe, Pets Welcome

Rocky Vines Wine Country Retreat w/ Fire Pit

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place, friendly and helpful hosts. "
Rocky Vines Wine Country Retreat w/ Fire Pit

2 Mi to Hollywood Casino: Charles Town Townhome!

3.5 star property
2 Mi to Hollywood Casino: Charles Town Townhome!

Harpers Ferry Apartment w/ Private Pool & Hot Tub!

3.0 star property
6.0 out of 10, (1)
"This is a hard review to write. The outdoor space included with this rental is awesome - gorgeous gardens, refreshing pool, nice tiki bar area. The only downside is that route 340 is VERY close, so there is a lot of highway noise (including loud truck brakes). We nevertheless enjoyed the outdoor amenities. The apartment is a true basement; if you are over 6 feet tall you may hit your head on a couple of door jambs. And you hear quite a bit of walking noise from above. We were also frustrated...
Harpers Ferry Apartment w/ Private Pool & Hot Tub!

Historic Townhome in Downtown Shepherdstown!

3.0 star property
Historic Townhome in Downtown Shepherdstown!

Charles Town Townhome: 9 Mi to Harpers Ferry

3.0 star property
Charles Town Townhome: 9 Mi to Harpers Ferry

Brunswick Retreat < 1 Mi to Potomac River!

3.0 star property
Brunswick Retreat < 1 Mi to Potomac River!

Close to IAD Sauna Wellness

2.0 star property
Close to IAD Sauna Wellness

Balcony & Pool Access: Modern Gainesville Home

3.5 star property
The price is NT$4,814
NT$13,208 total
includes taxes & fees
Aug 19 - Aug 20
Balcony & Pool Access: Modern Gainesville Home

Central Front Royal Getaway on Main Street!

3.0 star property
Central Front Royal Getaway on Main Street!

Townhome in Leesburg Historic District!

3.5 star property
Townhome in Leesburg Historic District!

Peaceful Riverfront Retreat w/ Yoga & Art Studio!

3.0 star property
Peaceful Riverfront Retreat w/ Yoga & Art Studio!

Cozy Inwood Apartment: History, Hiking & Wine!

3.0 star property
Cozy Inwood Apartment: History, Hiking & Wine!

< 1 Mi to Wineries: Quaint & Cozy Waterford Studio

3.0 star property
< 1 Mi to Wineries: Quaint & Cozy Waterford Studio
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

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You can choose from 21 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: Family Farmhouse Inn: 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 21 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.