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Winston's Cafe

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

Traveller rating
Traveller type
Time of year
Showing 52: English reviews
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
66 reviews
38 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
120 reviews
47 restaurant reviews
common_n_restaurant_reviews_1bd8 81 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
21 reviews
15 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 22 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 11 helpful votes
1 of 5 bubbles Reviewed 17 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 9 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
76 reviews
47 restaurant reviews
common_n_restaurant_reviews_1bd8 25 helpful votes
4 of 5 bubbles 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 (i prefer to share those experiences) so ducked inside. I sat at the bar and... More 

1 Thank t c
Virginia Beach, Virginia
Level Contributor
32 reviews
7 restaurant reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
5 of 5 bubbles 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 the area.

Thank Matze_Brandt
Level Contributor
170 reviews
91 restaurant reviews
common_n_restaurant_reviews_1bd8 58 helpful votes
5 of 5 bubbles 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

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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
USD 20
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
  • 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?