23 Best Wineries In Chestertown

23 restaurants available nearby

How are Featured results ranked

A photo of Bacco Italian and Wine Bar restaurant

1. Bacco Italian and Wine Bar

4.8

Exceptional(1563)

$$$$

• Winery • Bel Air

Booked 54 times today

As always, wonderful experience. Food, drinks, service, atmosphere—outstanding. Sorry we once again closed the place down. :-)

A photo of Cooper's Hawk Winery & Restaurant - Annapolis, MD restaurant

2. Cooper's Hawk Winery & Restaurant - Annapolis, MD

4.5

Awesome(8004)

$$$$

• Winery • Annapolis

Booked 119 times today

Samiyah was great had a wonderful time for our first time

A photo of Tagliata Restaurant restaurant

3. Tagliata Restaurant

4.7

Exceptional(3299)

$$$$

• Winery • Harbor East

Booked 65 times today

The food and service were outstanding. The menu offers a great variety in both food and beverage choices. We will most certainly be repeat diners when we next have the chance.

A photo of Rusty Scupper - Baltimore restaurant

4. Rusty Scupper - Baltimore

4.8

Exceptional(9165)

$$$$

• Winery • Inner Harbor

Booked 53 times today

It had been quite some time since I was there, it was terrific!

A photo of The Capital Grille - Baltimore restaurant

5. The Capital Grille - Baltimore

4.8

Exceptional(4166)

$$$$

• Winery • Downtown

Booked 56 times today

Everything was absolutely wonderful. My server was actually training someone he was wonderful and I see why he’s a trainer.

6. Love, Pomelo

new

4.8

Exceptional(6)

$$$$

• Winery • Canton

Booked 31 times today

I loved the vibe at LP! The atmosphere is intimate without feeling crowded. The mix of flavors in the barbabietole were like a party for the palate! I really liked the service pace, attentive and there when needed but not in our space. Highly recommend, everything was delicious and the staff are great! 💯

7. The Wardroom

4.8

Exceptional(415)

$$$$

• Winery • Easton

Booked 16 times today

One of the best meals in a longtime. Incredible service and amazing food. New favorite in Easton.

8. Limoncello

4.6

Exceptional(1586)

$$$$

• Winery • St Michaels / Tilghman Island

Booked 23 times today

By far, this is one of the best restaurant in Saint Michael’s.

A photo of Ava’s Pizzeria & Wine Bar - St. Michaels restaurant

9. Ava’s Pizzeria & Wine Bar - St. Michaels

4.7

Exceptional(302)

$$$$

• Winery • St Michaels / Tilghman Island

Booked 15 times today

We had a wonderful experience at Ava’s Pizzeria & Wine Bar! The food was absolutely delicious, and our host went above and beyond to make us feel welcome and well taken care of. The service was outstanding, and the overall atmosphere made our evening truly special. Everything was excellent from start to finish. We will definitely be back. Highly recommended! ¡Tuvimos una experiencia maravillosa en Ava’s Pizzeria & Wine Bar! La comida estuvo absolutamente deliciosa y nuestro anfitrión nos brindó una atención excepcional, haciéndonos sentir muy bienvenidos y atendidos en todo momento. El servicio fue impecable y el ambiente hizo que nuestra velada fuera realmente especial. Todo estuvo excelente de principio a fin. ¡Sin duda volveremos! ¡Totalmente recomendado!

A photo of Latitude 38 Annapolis restaurant

10. Latitude 38 Annapolis

4.0

Excellent(452)

$$$$

• Winery • Annapolis

Booked 4 times today

Even amid the construction, the restaurant was fantastic! We’ll be back.

Best Wineries in Chestertown

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23 restaurants available nearby

1. Bacco Italian and Wine Bar

2. Cooper's Hawk Winery & Restaurant - Annapolis, MD

3. Tagliata Restaurant

4. Rusty Scupper - Baltimore

5. The Capital Grille - Baltimore

6. Love, Pomelo

7. The Wardroom

8. Limoncello

9. Ava’s Pizzeria & Wine Bar - St. Michaels

10. Latitude 38 Annapolis

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