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Winston's Cafe

$$ - $$$
American, Bar
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1412 Greenbrier Pkwy Ste 133, Chesapeake, VA 23320-2834
+1 757-420-1751
11:00 - 02:00
Closed now
See all hours
Sun 09:00 - 02:00
Mon - Sat 11:00 - 02:00
More Info
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54 Reviews from our TripAdvisor Community

Traveller rating
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Time of year
Showing 54: English reviews
Berea, Kentucky
Level Contributor
209 reviews
102 restaurant reviews
common_n_restaurant_reviews_1bd8 49 helpful votes
3 of 5 bubbles Reviewed 2 days ago NEW

The food was good for bar food. The service was good as well. We had a drink and they were pretty good too. Nothing special, but nothing wrong either. Dinner entrees not served to about 1730.

Thank Patty L G
Chesapeake, Virginia
Level Contributor
62 reviews
33 restaurant reviews
common_n_restaurant_reviews_1bd8 15 helpful votes
5 of 5 bubbles Reviewed 17 February 2017 via mobile

The food, drinks, and service were great. Very busy on a Friday night and we got the last table, just before 6pm. My colleague ordered the English Dip. It was cooked to perfection, and was a good size portion. I got the Cajun Ahi Tuna, it was also cooked perfectly and had a nice side sauce. Stephanie took good category... More 

Thank Purple_Eagle_Richard
Chesapeake, Virginia
Level Contributor
58 reviews
49 restaurant reviews
common_n_restaurant_reviews_1bd8 18 helpful votes
5 of 5 bubbles Reviewed 13 October 2016

I have been here for lunch and really enjoyed the food and the service. The bartender makes great drinks and they have a greatly priced happy hour.

Thank mzlita
Chesapeake, Virginia
Level Contributor
67 reviews
39 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
5 of 5 bubbles Reviewed 13 September 2016

good food ,open mic nights are good some great singers. nightly specials are great prime rib weds have to try their mac and cheese

Thank dabigdog123
South Floorida
Level Contributor
122 reviews
47 restaurant reviews
common_n_restaurant_reviews_1bd8 82 helpful votes
4 of 5 bubbles Reviewed 5 September 2016

Great food and service for lunch or dinner. Their specials are well thought out and taste great. I have eaten here twice and tried for a third time but since this small place was full I had to more on.

Thank Breter
Saint Paul, Minnesota
Level Contributor
26 reviews
14 restaurant reviews
common_n_restaurant_reviews_1bd8 15 helpful votes
5 of 5 bubbles Reviewed 13 August 2016

Needed a nice little place to go on a Saturday for a late lunch and this place hit the spot. I cannot stop raving about their Cranberry chicken salad. Most places put too many onions in their salad and this place didn't put any. It was amazing and delicious. The kids enjoyed their mac and cheese and grilled cheese meals.... More 

Thank C S
Chesapeake, Virginia
Level Contributor
22 reviews
16 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 21 July 2016 via mobile

My wife likes to go to national chain restaurants, two of which are next door to the little pub that we found on their left, a gem I have been going to since moving to Chesapeake. As I said, Winston's is a little pub but the full bar and menu is not lacking. The owner (Jeff) and staff are extremely... More 

Thank Gibraltar2014
Norfolk, Virginia
Level Contributor
16 reviews
16 restaurant reviews
common_n_restaurant_reviews_1bd8 12 helpful votes
1 of 5 bubbles Reviewed 16 July 2016

My son, my bride and I decided to go out Friday evening and wanted to try somewhere different.We were in the Greenbrier section of Chesapeake and looked thru different restaurants on the phone when we decided to try Winston's Cafe. It was tucked out of the way, in a strip mall, but that wasn't going to deter us. It should... More 

Thank r s
Lexington, Kentucky
Level Contributor
35 reviews
18 restaurant reviews
common_n_restaurant_reviews_1bd8 13 helpful votes
4 of 5 bubbles Reviewed 8 July 2016 via mobile

In town for my family's annual trip to visit family, I always look for local places to eat. After reading up on Winston's, we (wife, 5yo daughter and 7yo son) decided to give it a try. We had an order of potato chips covered in cheese and bacon for an app - yummy. I ordered the French dip, and would... More 

Thank David K
chesapeake, virginia
Level Contributor
99 reviews
60 restaurant reviews
common_n_restaurant_reviews_1bd8 26 helpful votes
4 of 5 bubbles Reviewed 13 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 (i prefer to share those experiences) so ducked inside. I sat at the bar and... More 

1 Thank t c

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Restaurant Details

Rating summary
  • Food
    4 of 5 bubbles
    4 of 5 bubbles
  • Value
    4 of 5 bubbles
    4 of 5 bubbles
Average prices
American, Bar
Lunch, Dinner, After-hours, Drinks
Restaurant features
Seating, Waitstaff, Serves Alcohol, Takeout, Television, Wheelchair Accessible
Good for
Cheap Eats, Bar Scene, Child-friendly
Open Hours
09:00 - 02:00
11:00 - 02:00
11:00 - 02:00
11:00 - 02:00
11:00 - 02:00
11:00 - 02:00
11:00 - 02:00
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

Questions & Answers

Questions? Get answers from Winston's Cafe staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?