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Winston's Cafe

1412 Greenbrier Pkwy Ste 133, Chesapeake, VA 23320-2834
+1 757-420-1751
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  • Excellent54%
  • Very good26%
  • Average13%
  • Poor4%
  • Terrible3%
Travellers talk about
“french dip” (5 reviews)
“prime rib” (6 reviews)
“sandwich” (5 reviews)
Closes in 5 min
American, Bar
$$ - $$$
1412 Greenbrier Pkwy Ste 133, Chesapeake, VA 23320-2834
All Details
Write a ReviewReviews (65)
Traveller rating
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21 - 30 of 65 reviews

Reviewed 14 June 2016 via mobile

Ive been in the area for awhile but never really came in here. I actually intended to stop next door (Ruby Tuesday) for a small dinner but saw a sign outside about $5.00 burger night. Being solo, i wasnt really looking for a foodie place...More

1  Thank t c
Reviewed 23 December 2015 via mobile

It's a very good Place to hang out. The staff is very friendly. Each night they have different live music. It starts at 8 p.m. The food is very good and they have every day a special. It is one of my favourit bars in...More

Thank Matze_Brandt
Reviewed 22 December 2015

This is my favorite low key spot to go chill and eat. They have live music some nights and the food is normally really good. The dips come out way too hot so be careful, but enjoy.

Thank Daniel s
Reviewed 18 December 2015

First of all, I've been going to Winston's for at least 20+ years. Been a few different owners the last few years but the food has stayed consistently excellent. That being said, while I love the food (the French Dip for lunch is awesome), the...More

Thank Phrankenstrat
Reviewed 15 November 2015

I sampled the Friend Dip. It was excellent. Medium pink meant with bread that was perfectly crusty. Just the right package. My burger was juicy, the bacon was crispy the bum was crusty. What more could you ask? It was a great meal!

Thank StayCationNC
Reviewed 24 July 2015

The last time I visited Winston's was around November 2014. I had already given up on the place, as with numerous past visits, the service was beyond mediocre. I decided to give the place an additional try, after having given the place numerous chances over...More

Thank ScottTravelsTheWorld
Reviewed 30 March 2015

We arrived after 9 pm and ordered entrees. Chicken salad was outstanding! This is a bar but was not loud or too crowded. Service was good.

Thank agapeMom
Reviewed 15 March 2015 via mobile

A small restaurant bar with very pleasant service and decent food. Live music on weekends. Not the newest or cleanest, but a pleasant place.

Thank Rusty B
Reviewed 25 February 2015

Found this place as I was driving by and went in for dinner. At first things seemed to be going good. Once I ordered a Coke to drink my Server seemed to chance her attitude since I wasn't drinking. It took me a while to...More

1  Thank Douglas M
Reviewed 9 February 2015

I have said before that this is a great burger. It is IF it's properly cooked which this time it was not. However the french dip sandwich I shared was a delicious mix of rare roast beef and the crunch of the bread that was...More

Thank StayCationNC
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Restaurant Details

Rating summary
  • Food
  • Value
Average prices
American, Bar
Dinner, Lunch, After-hours, Drinks
Restaurant features
Seating, Waitstaff, Television, Wheelchair Accessible, Serves Alcohol, Takeout
Good for
Bar Scene, Child-friendly
Open Hours
9:00 AM - 2:00 AM
11:00 AM - 2:00 AM
11:00 AM - 2:00 AM
11:00 AM - 2:00 AM
11:00 AM - 2:00 AM
11:00 AM - 2:00 AM
11:00 AM - 2:00 AM
Location and Contact Information
  • Address: 1412 Greenbrier Pkwy Ste 133, Chesapeake, VA 23320-2834
  • Location: United States  >  Virginia (VA)  >  Chesapeake
  • Phone Number: +1 757-420-1751
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