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  4. Lexington
  5. Winchester

Best Date Night Restaurants in Winchester

Price
Cuisine
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Top Rated
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54 restaurants available nearby

How are Featured results ranked

A photo of The V at The Vine restaurant
4.3
Awesome(249)
$$$$
• Contemporary American • Lexington
Booked 3 times today
⭐️⭐️⭐️⭐️⭐️ We went on a date night, and this was our first time here. We sat on the patio on a beautiful fall night overlooking the skyline of Lexington. (And although patio heaters were provided, they were not needed. Perfect weather!) Our first impression was the incredible view, but little do we know, the best was yet to come. Chef Ben Alexander prepared amazing food for us. "To die for" mussels, "slap your mama" Wagyu, roasted vegetables that would make you fall off your chair, and the masala was so creamy and delicious. From the hostess to the wait staff, so courteous and attentive. Thank you for a beautiful date night. Can't wait to come back! ⭐️⭐️⭐️⭐️⭐️
A photo of Merrick Inn restaurant
4.7
Exceptional(5363)
$$$$
• Contemporary Southern • Lexington
Booked 54 times today
Absolutely fantastic. Pricey but worth it. Steak was perfection. Wine list was great.
A photo of Tony's of Lexington restaurant
4.8
Exceptional(5629)
$$$$
• Steakhouse • Lexington
Booked 69 times today
James and his SA Jake were fabulous. As someone who works in fine dining I was impressed at how smoothly and effortlessly we were taken care of. Everything coursed and cleared perfectly. Very thankful for their service!
A photo of Carson's at Andover restaurant
4.7
Exceptional(2187)
$$$$
• American • Lexington
Booked 96 times today
My girlfriend and I always enjoy food and service is always great and we enjoy the views. We will be returning in the future
A photo of Giuseppe's Ristorante Italiano restaurant
4.8
Exceptional(5223)
$$$$
• Italian • Lexington
Booked 62 times today
I’ve been hearing about how great this restaurant is but finally went for my daughter’s 15th birthday. It was excellent! The service was perfect, and friendly. The food was all delicious, timely and hot. There was a musician performing jazz and we could still hear one another. I can’t wait to go again!
A photo of Frank and Dino's restaurant
4.8
Exceptional(2053)
$$$$
• Italian • Lexington
Booked 24 times today
One of our favorite places to dine, never disappointed.
A photo of Carson's on Main restaurant
4.8
Exceptional(7270)
$$$$
• American • Lexington
Booked 117 times today
I’m from Buffalo NY and Visiting my son and daughter in law and each time I come down we dine here. The ambiance is incredible, the drinks are great, the food is amazingly delicious and the service is outstanding! Everyone is incredible, everything is always, always on point. We DEFINITELY recommend this establishment to anyone and everyone! I’m looking forward to our next visit! Can’t say enough good things about Carson’s!
A photo of ItalX restaurant
4.7
Exceptional(890)
$$$$
• Italian • Lexington
Booked 23 times today
This is our new favorite restaurant! We’ve eaten at ItalX three times in the past week. The homemade pastas and sauces are amazing, and the service is great. I highly recommend the chicken piccata, and veal marsala.
A photo of Palmers Fresh Grill restaurant
4.5
Awesome(1985)
$$$$
• Seafood • Lexington
Booked 9 times today
Food was amazing and our server was very attentive. We had the calamari, shrimp and grits and the steak and fries. Everything was perfect!
A photo of OBC Kitchen restaurant
4.8
Exceptional(5202)
$$$$
• American • Lexington
Booked 79 times today
Literally the best brunch of my life. We loved every single thing we ordered

See what locals rave about

From verified diners like you
From verified diners like you
  • Celia
    Hawaii •2 reviews
    5.0
    Dined 2 days ago
    I’ve been hearing about how great this restaurant is but finally went for my daughter’s 15th birthday. It was excellent! The service was perfect, and friendly. The food was all delicious, timely and hot. There was a musician performing jazz and we could still hear one another. I can’t wait to go again!
    More info
    Giuseppe's Ristorante Italiano$$$$• Italian• Lexington
    •
    4.8
  • Lawrence
    Central Kentucky •19 reviews
    5.0
    Dined 2 days ago
    I’m from Buffalo NY and Visiting my son and daughter in law and each time I come down we dine here. The ambiance is incredible, the drinks are great, the food is amazingly delicious and the service is outstanding! Everyone is incredible, everything is always, always on point. We DEFINITELY recommend this establishment to anyone and everyone! I’m looking forward to our next visit! Can’t say enough good things about Carson’s!
    More info
    Carson's on Main$$$$• American• Lexington
    •
    4.8
  • DavidGold
    Central Kentucky •8 reviews
    5.0
    Dined 2 days ago
    My girlfriend and I always enjoy food and service is always great and we enjoy the views. We will be returning in the future
    More info
    Carson's at Andover$$$$• American• Lexington
    •
    4.7
  • johnGold
    Chicago / Illinois •17 reviews
    5.0
    Dined 3 days ago
    ⭐️⭐️⭐️⭐️⭐️ We went on a date night, and this was our first time here. We sat on the patio on a beautiful fall night overlooking the skyline of Lexington. (And although patio heaters were provided, they were not needed. Perfect weather!) Our first impression was the incredible view, but little do we know, the best was yet to come. Chef Ben Alexander prepared amazing food for us. "To die for" mussels, "slap your mama" Wagyu, roasted vegetables that would make you fall off your chair, and the masala was so creamy and delicious. From the hostess to the wait staff, so courteous and attentive. Thank you for a beautiful date night. Can't wait to come back! ⭐️⭐️⭐️⭐️⭐️
    More info
    The V at The Vine$$$$• Contemporary American• Lexington
    •
    4.3
  • Michelle
    Chicago / Illinois •4 reviews
    5.0
    Dined on Oct 19, 2026
    This was by far one of the loveliest dining experiences I’ve ever had. What a delight to have Millstone here in the Bluegrass. We had the salmon and the braised short ribs. Both were exceptional! The cocktails were divine too. Ricky was both attentive and hospitable. We can’t wait to return!
    More info
    Millstone$$$$• American• Lexington
    •
    4.8
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