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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
Open now
See all hours
Sun 09:00 - 02:00
Mon - Sat 11:00 - 02:00
More Info
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56 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Showing 56: English reviews
Asheville, North Carolina
Level Contributor
137 reviews
64 restaurant reviews
common_n_restaurant_reviews_1bd8 32 helpful votes
Reviewed 3 days ago NEW

Just like the title says. I had the French Dip, it was really good. Could have had some more au jus up front so I didn't have to ask for more, but that's the only knock I have on it. Service was good, quick, attentive.

Thank Bonzaiflyer
Virginia Beach, Virginia
Level Contributor
195 reviews
112 restaurant reviews
common_n_restaurant_reviews_1bd8 71 helpful votes
Reviewed 1 week ago via mobile

Having heard about Prime Rib night we thought we would explore defined out about it. My prime rib was nicely prepared. Came with two sides. The end of season vegetable broccoli. There are many starches in the choices. My prime rib was a little fatty. My husband has sweet tea and I had water.

Thank GloriaMunday
Berea, Kentucky
Level Contributor
230 reviews
117 restaurant reviews
common_n_restaurant_reviews_1bd8 50 helpful votes
Reviewed 4 weeks ago

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
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
59 reviews
50 restaurant reviews
common_n_restaurant_reviews_1bd8 18 helpful votes
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
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
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
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
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
18 reviews
17 restaurant reviews
common_n_restaurant_reviews_1bd8 12 helpful votes
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

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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
Bar Scene, Cheap Eats, 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?