We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winston's Cafe

₹₹ - ₹₹₹American,
1412 Greenbrier Pkwy Ste 133, Chesapeake, VA 23320-2834
+1 757-420-1751
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
  • Excellent54%
  • Very good25%
  • Average14%
  • Poor4%
  • Terrible3%
Travellers talk about
“french dip” (5 reviews)
“prime rib” (6 reviews)
“ahi tuna” (2 reviews)
Open Now
American, Bar
₹₹ - ₹₹₹
1412 Greenbrier Pkwy Ste 133, Chesapeake, VA 23320-2834
All Details
Write a Review
JPMiles / Payback Arrow
JPMiles / Payback Arrow
Reviews (64)
Traveller rating
Traveller type
Time of year

1 - 10 of 64 reviews

Reviewed 5 March 2018

Frankie was an excellent server and the food was great as well. It's a small place so get there early to get a seat but the local specials were wonder.

Thank vacritter2000
Reviewed 18 February 2018

I'm afraid to say too much, or there won't be a seat next time I go. But the atmosphere is fantastic, and the Caesar salad with a bit of salmon on top is my favorite. And Taco Tuesday specials.

Thank CapallGlas
Reviewed 12 January 2018

We got home late from work, too tired to cook. "Let's go to Winston's!", my husband said. How could I say no? I had a delicious salmon dinner and my husband had his usual burger, which he loves. Dinner was excellent and we look forward...More

Thank MargaretR8
Reviewed 6 November 2017

We usually go here for lunch during the week. Not a huge restaurant but I like that. Always friendly staff and good food!

Thank Loretta B
Reviewed 24 October 2017 via mobile

French dip was great fries great and the service was spot on. Reportedly great pasta dishes too! Enjoy!

Thank David M
Reviewed 14 October 2017 via mobile

Lovely local joint, fun bar vibes, EXCELLENT AHI TUNA BITES and amazing service. The crowd was fun, football on the tv, great food. The French onion soup was awesome.

Thank Erin G
Reviewed 4 October 2017

Prime Rib was done pretty good... comes with two sides. Regular price for a 10oz prime rib is around $18 but during the special night comes down to $12.99! A great place to have dinner with your love ones.

Thank bubbafel
Reviewed 19 August 2017 via mobile

A small but extremely friendly cafe with delicious food surrounded by extremely mediocre (at best) chain restaurants. We stopped here for a late lunch on a day of travel. My sandwich consisted of freshly sliced turkey with crispy flavorful bacon with melted cheese and tomato...More

Thank SteveN0729
Reviewed 24 April 2017

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
Reviewed 20 April 2017 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....More

Thank GloriaMunday
Nearby HotelsSee all 42 hotels in Chesapeake
Homewood Suites by Hilton Chesapeake-Greenbrier
426 reviews
.68 km away
Hilton Garden Inn Chesapeake/Greenbrier
521 reviews
.74 km away
Hyatt Place Chesapeake/Greenbrier
671 reviews
.81 km away
Fairfield Inn & Suites Chesapeake
220 reviews
.86 km away
Nearby Restaurants
284 reviews
.43 km away
Black Pelican
200 reviews
.23 km away
Pop's Diner Co.
205 reviews
.28 km away
Nearby Attractions
Greenbrier Mall
28 reviews
.09 km away
Relax the Feet
46 reviews
.86 km away
Cinema Cafe
55 reviews
.09 km away
Cloud 9 Trampoline Park
53 reviews
1.54 km away
Questions & Answers
Get quick answers from Winston's Cafe staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines
Improve this listing

Restaurant Details

Rating summary
  • Food
  • Value
Average prices
US$ 20
American, Bar
Dinner, Lunch, After-hours, Drinks
Restaurant features
Seating, Waitstaff, Television, Wheelchair Accessible, Serves Alcohol, Takeout
Good for
Child-friendly, Bar Scene
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
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more. Claim Your Listing