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Best Contemporary American Restaurants in Winchester

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11 restaurants available nearby

How are Featured results ranked

A photo of Granddam restaurant
4.5
Awesome(679)
$$$$
• Contemporary American • Lexington
Booked 18 times today
Excellent cuisine in particular the mushroom appetizer and the striped bass entree Both perfectly prepared. A must the next time in Lexington! Service was excellent too.
A photo of Blue Heron Steakhouse restaurant
4.7
Exceptional(2422)
$$$$
• Contemporary American • Lexington
Booked 23 times today
Excellent steak and side dishes; could cut the filet with a fork; great service in a low key atmosphere; great place for conversation
A photo of The V at The Vine restaurant
4.3
Awesome(249)
$$$$
• Contemporary American • Lexington
Booked 12 times today
⭐️⭐️⭐️⭐️⭐️ We went on a date night, and this was our first time here. We sat on the patio on a beautiful fall night overlooking the skyline of Lexington. (And although patio heaters were provided, they were not needed. Perfect weather!) Our first impression was the incredible view, but little do we know, the best was yet to come. Chef Ben Alexander prepared amazing food for us. "To die for" mussels, "slap your mama" Wagyu, roasted vegetables that would make you fall off your chair, and the masala was so creamy and delicious. From the hostess to the wait staff, so courteous and attentive. Thank you for a beautiful date night. Can't wait to come back! ⭐️⭐️⭐️⭐️⭐️
A photo of Coles 735 Main restaurant
4.8
Exceptional(3773)
$$$$
• Contemporary American • Lexington
Booked 31 times today
The food & service were outstanding! The Filet Oscar just melted in your mouth. One suggestion would be is to add some sort of lighting on the tables. It was very hard to read menus, we had to use the flashlights on our phones to read the menu and I noticed a few other people at other tables had to do the same. A candle or soft table lamp would help and also add to the ambience. Thank you
A photo of Bella Cafe & Grille - Hamburg restaurant
4.9
Exceptional(92)
$$$$
• Contemporary American • Lexington
Booked 14 times today
Rocky was a terrific server and mixologist. Good was superb and atmosphere was welcoming.
A photo of Bella Cafe & Grille (Fountains at Palomar) restaurant
4.9
Exceptional(494)
$$$$
• Contemporary American • Lexington
Booked 17 times today
There isn't a better staff in town. Always kind and friendly. They make us feel welcomed and appreciated.
A photo of Heirloom - Midway restaurant
4.8
Exceptional(2507)
$$$$
• Contemporary American • Midway
Booked 24 times today
Lovely restaurant. Crab cakes and tea smoked duck were excellent. Fried chicken and tuna tartare were good. Service was excellent
A photo of AZUR Restaurant & Patio restaurant
4.6
Exceptional(2219)
$$$$
• Contemporary American • Lexington
Booked 6 times today
Azur continues to provide delicious food paired with excellent service.
A photo of Castle Farm restaurant
4.5
Awesome(4351)
$$$$
• Contemporary American • Lexington
Booked 35 times today
Great menu, food selection and quality, service was great!
A photo of Holly Hill Inn restaurant
4.7
Exceptional(1470)
$$$$
• Contemporary American • Midway
Booked 18 times today
Awesome experience…… atmosphere, food quality, service. Highly recommend to anyone looking to celebrate a special occasion.

See what locals rave about

From verified diners like you
From verified diners like you
  • Nancy
    Central Kentucky •2 reviews
    5.0
    Dined 3 days ago
    The food & service were outstanding! The Filet Oscar just melted in your mouth. One suggestion would be is to add some sort of lighting on the tables. It was very hard to read menus, we had to use the flashlights on our phones to read the menu and I noticed a few other people at other tables had to do the same. A candle or soft table lamp would help and also add to the ambience. Thank you
    More info
    Coles 735 Main$$$$• American• Lexington
    •
    4.8
  • Daryl
    Fort Lauderdale •14 reviews
    5.0
    Dined 5 days ago
    Excellent steak and side dishes; could cut the filet with a fork; great service in a low key atmosphere; great place for conversation
    More info
    Blue Heron Steakhouse$$$$• Steakhouse• Lexington
    •
    4.7
  • KeithGold
    Central Kentucky •80 reviews
    5.0
    Dined 6 days ago
    There isn't a better staff in town. Always kind and friendly. They make us feel welcomed and appreciated.
    More info
    Bella Cafe & Grille (Fountains at Palomar)$$$$• American• Lexington
    •
    4.9
  • Kevin
    Jacksonville / Northeast Florida •1 review
    5.0
    Dined on Oct 28, 2026
    Rocky was a terrific server and mixologist. Good was superb and atmosphere was welcoming.
    More info
    Bella Cafe & Grille - Hamburg$$$$• American• Lexington
    •
    4.9
  • johnGold
    Chicago / Illinois •17 reviews
    5.0
    Dined on Oct 24, 2026
    ⭐️⭐️⭐️⭐️⭐️ We went on a date night, and this was our first time here. We sat on the patio on a beautiful fall night overlooking the skyline of Lexington. (And although patio heaters were provided, they were not needed. Perfect weather!) Our first impression was the incredible view, but little do we know, the best was yet to come. Chef Ben Alexander prepared amazing food for us. "To die for" mussels, "slap your mama" Wagyu, roasted vegetables that would make you fall off your chair, and the masala was so creamy and delicious. From the hostess to the wait staff, so courteous and attentive. Thank you for a beautiful date night. Can't wait to come back! ⭐️⭐️⭐️⭐️⭐️
    More info
    The V at The Vine$$$$• Contemporary American• Lexington
    •
    4.3
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