Skip to content

Top recommendations from locals

From sightseeing to hidden gems, find out what makes the city unique with the help of the locals who know it best.
Museum
“Museum & plantation home showcasing 18th-century art, a mini-house collection & regional history. ”
  • 14 locals recommend
Entertainment
“Comedy shows, live music, food and drink. Check out their entertainment schedule.”
  • 5 locals recommend
Museum
“Spark curiosity & inspire learning through exploration & creative play ! All ages will discover playful learning through hands-on, interactive exhibits at the Shenandoah Valley Discovery Museum! Discover the fun ... birthday parties for all ages, after hours rentals, overnights in the museum, summer camps June-August, School Field Trips & Programs! Open year around - Tues-Sat 9a-5p, Sun 1-5p, Mon -Closed!”
  • 6 locals recommend
Park
“Things to do for the whole family including running trails, disc golf, fitness facilities, with an outdoor pool (summer) and indoor pool. We provide you with the up to date calendar.”
  • 5 locals recommend
Bar
$$
“Great atmosphere, live music, great food and drinks. Always lively on the weekends. Trivia Nights.”
  • 8 locals recommend
Bakery
“Freshly made in-house biscuts, local fried apples, and some of the best BBQ ever! ”
  • 5 locals recommend
Bar
“Fish & chips! Among other authentic- English pub fare. Impressive beer selection. Has a "public hall" feel downstairs, cushy chairs on the landing upstairs. ”
  • 5 locals recommend
Bar
“This restaurant boasts 50 craft beers along with 50 gourmet burgers. They have "beer flights" and the burgers are a great deal with a healthy side of fries for around $10.00”
  • 7 locals recommend
Cafe
“Great owner, cool vibe and some of the best coffee in town, and there are lots. Plus, vintage interiors and records and occassionally live music!”
  • 4 locals recommend
Miscellaneous Shop
“(40min) Old Town Winchester, a shopping and dining hub, is home to Stonewall Jackson's Headquarters Museum, featuring Civil War memorabilia. To the east, vast Jim Barnett Park includes a lake, an arboretum and sports facilities.”
  • 8 locals recommend
Museum
“George Washington started his professional career in Winchester as a Land Surveyor. His office here (also known as the Adam Kurtz House, built 1757) was used during construction of Fort Loudoun.”
  • 4 locals recommend
Restaurant
$$
“The de facto standard for excellent Thai in Winchester--everyone I know agrees they are great, with generous portions, friendly service, and a kid-favorite free dessert "smile". This is located on the walking mall though there is a 2nd location on Pleasant Valley which is equally good, just more of a strip mall experience. ”
  • 4 locals recommend
Bar
$$
“Decent burgers, domestic beer on tap. Pleasant patio scene in daytime. There aren't many places to dance in Winchester. Brewbaker's is one. Noisy sweaty late night destination. ”
  • 2 locals recommend
Food
“ Another brewery! One of four in Winchester...and counting! The owners are super pleasant. Sit at the bar, and you'll probably meet them. The beer is really good. Try the smoky Chipotle-infused porter. You can take home a can, they'll can you one fresh while you sip.”
  • 3 locals recommend
Grocery or Supermarket
“Sadly, there is no walking to the grocery from Wickham House, not yet anyway. Until we get a WholeFoods (or a Wegman's...or a Trader Joe's), there is Martin's. It's basically a big Giant Foods. The produce is good, if pricey. There are several locations. This is the one closest to the University. ”
  • 2 locals recommend

Top restaurants

Bar
“Great atmosphere, live music, great food and drinks. Always lively on the weekends. Trivia Nights.”
  • 8 locals recommend
Bakery
“Freshly made in-house biscuts, local fried apples, and some of the best BBQ ever! ”
  • 5 locals recommend
Bar
“This restaurant boasts 50 craft beers along with 50 gourmet burgers. They have "beer flights" and the burgers are a great deal with a healthy side of fries for around $10.00”
  • 7 locals recommend
Restaurant
“The de facto standard for excellent Thai in Winchester--everyone I know agrees they are great, with generous portions, friendly service, and a kid-favorite free dessert "smile". This is located on the walking mall though there is a 2nd location on Pleasant Valley which is equally good, just more of a strip mall experience. ”
  • 4 locals recommend
Bar
“Decent burgers, domestic beer on tap. Pleasant patio scene in daytime. There aren't many places to dance in Winchester. Brewbaker's is one. Noisy sweaty late night destination. ”
  • 2 locals recommend
Restaurant
“Delicious cuisine featuring sushi and Thai. Within walking distance, has a bar. ”
  • 4 locals recommend
Meal Delivery
“Best Italian in Winchester, not for the location, but the food. Love this place more every visit. Their name couldn't be more perfect! Authentic food and friendly staff who welcome you into their family and from experience will make it however you like. You know--it's more like a discussion with that Italian uncle who asks everyone what they REALLY want before he recedes into his kitchen to show you how much he loves you. Menu, schmenu.”
  • 1 local recommends
Restaurant
“Delicious pizza, house made sangria, a brewery upstairs. This place has it all!”
  • 1 local recommends

Get to know Winchester

Explore more on Airbnb

Experiences in Winchester