"Ten outta ten would stay here again and again and again! Plenty of eatery options nearby, great staff and super quiet! Clean and fun! Had an awesome time!"
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.
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.
Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.
You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants.
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theater.
Winchester is a lovely town. Lots of history & beautiful buildings. Good restaurants & shopping. Easy on & off the Interstate. Top of the line hospital. Beautiful surroundings
Ruth
10.0/10
Excellent
We always stop in Winchester on our way to and from NY-NC. Old Town is great! Lots of history in this area.
michael
10.0/10
Excellent
Walking the streets to explore a richness of architecture. The Old Town walking mall is a delight
william
10.0/10
Excellent
My husband and I really like the Old Town area (downtown pedestrian area). Great restaurants! Friendly folks! Unfortunately there is a Confederate memorial statue downtown which I find racist. Don't fete those who fought to preserve slavery.
Laurie
8.0/10
Good
The Old Town area and the Museum of the Shenandoah Valley are wort a visit.
Beverly
10.0/10
Excellent
Old Town is just a short drive away. Parking was easy and it is very pleasant with many nice restaurants. We went to El Centro and they allowed our dog on the patio and it was a great meal and atmosphere
Shaina
10.0/10
Excellent
Winchester is a nice small city in the Shenandoah region. The reason I stayed here was it was approximately halfway from my home in NJ and Asheville, NC - and had easy access off and on Rt. 81.
William
8.0/10
Good
Winchester seems to be a lovely town. Nearby Jim Barnett Park is fantastic, and the old town and pedestrian walk areas are well worth a visit.
Anonymous traveler
10.0/10
Excellent
Always enjoy Winchester. Most of the time for music at Blue Fox Billiards and Grill. Old Winchester is interesting downtown.
Ben
10.0/10
Excellent
I stay in Winchester annually. Love the downtown historic walking area with restaurants.
"The front desk and cleaning staff were really helpful when we lost our car key fob. They offered to call mechanics to create a duplicate and finally even found our lost one. "
"Very easy to get to. Across a Bar/Grill called Glory Days Grill. Very convenient. Very close to Winchester Old Town Mall but note everything closes at about 5 pm there. "
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! The majority of hotel reservations are refundable if you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To find more details about updating your trip to Winchester or cancelling it, click here.
What's the best budget-friendly hotel in Winchester?
What about the best place to stay near Bluemont Vineyard?
One of the top choices for your stay is Weddings at Highholdborne, located 1.6 mi (2.5 km) from Bluemont Vineyard, and this 3.5-star villa offers free breakfast and a restaurant. The Manor at Airmont and Airwell Bed and Breakfast are a couple of other good options within a few miles.
What's the best accommodation for a golf trip to Winchester?
Families will find kid-friendly activities in Winchester, and visitors give high marks for the shopping and top-notch restaurants. Scenic and vibrant, this city attracts tourists with its theaters and entertainment choices. In Winchester, there are 76 hotels and other accommodations to choose from. Find out more about 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.
