Restaurants near Holiday Inn Express Hotel & Suites Chestertown

Price

££
£££
££££

Cuisine

AmericanItalianSteakhouseSeafoodIndianJapanese

Top Rated

CharmingGood for business mealsGood for groupsGood for special occasionsGreat for brunchGreat for fine wines

Dining Options

All dining options

Delivery only

Takeaway only

Seating options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral toiletWheelchair access

34 restaurants available nearby

How are Featured results ranked

A photo of The Retriever Bar & The Decoy Bottle Shop restaurant

1. The Retriever Bar & The Decoy Bottle Shop

4.8

Exceptional(61)

££££Price: Moderate

• American • Chestertown

Booked 10 times today

The Retriever is a bar with great dining and the most extensive spirits selection around. Please note that even though we serve food we are classified as a bar and all guests must be 21 years old.

A photo of Bacco Italian and Wine Bar restaurant

2. Bacco Italian and Wine Bar

4.8

Exceptional(1340)

££££Price: Moderate

• Italian • Bel Air

Booked 26 times today

Sniff, Swirl, and Sip your way through top-rated wine and irresistible Italian food in a stylish, yet casual dining room and expansive bar. Serving authentic Italian dishes with an extensive wine list in addition to a self-serve wine system allowing guests to sample a variety of wines. Our story goes way back to the streets just outside of Naples, Italy. It is there that partners Gennaro and Ivano were infused with the skills for creative-yet-classic preparation and craftsmanship of a great Italian meal; and an overall experience that leaves you happy and content. Join us for an exceptional dining experience reminiscent of the stylish eateries and wine bars of Italy.

A photo of Osprey Point Restaurant restaurant

3. Osprey Point Restaurant

4.8

Exceptional(553)

££££Price: Expensive

• Contemporary American • Rock Hall

Booked 1 time today

Our fine dining restaurant has a reputation for being one of the best in Kent County. We pride ourselves on having a fresh seasonal menu, high quality ingredients and a chef that puts care into preparing every meal. The dining room's casual elegance will make you feel at home whether you are stepping off the dock or celebrating that special occasion. Please stop in for a drink and hors d'oeuvres at the bar or make a reservation for dinner. We welcome transient boaters throughout the season and offer free dockage while dining in our restaurant.

4. By The Docks

4.6

Exceptional(1974)

££££Price: Moderate

• Seafood • Essex

Booked 25 times today

Maryland is famous for it's crab cakes, and By The Docks is known for it's eight-ounce Colossal Jumbo Lump Crab Cake. Discover the fresh ingredients and outstanding seafood, steaks, and pasta's prepared by our chefs. Our menu includes various items from baby back ribs, slow roasted prime rib, hand cut steaks,and specialty sauteed dishes. Every sauce, soup and dressing is made from scratch. By The Docks welcomes families and large groups. Make reservations or call ahead for express carry out.

A photo of Michael's Cafe White Marsh/ Middle River restaurant

5. Michael's Cafe White Marsh/ Middle River

4.8

Exceptional(871)

££££Price: Moderate

• Contemporary American • White Marsh

Booked 18 times today

Reinvention and attention to detail have kept us in business for 40 years. We are honored to serve this community from this location since 2019 with many more happy years to come. See what our team, led by Chef Fabricio and our General Manager Josh, has to offer you. This restaurant is our home and we treat our guests with this philosophy in mind. Thank you!

A photo of Amalfi Coast Italian + Wine Bar restaurant

6. Amalfi Coast Italian + Wine Bar

4.8

Exceptional(964)

££££Price: Moderate

• Italian • Stevensville

Booked 9 times today

Benvenuti! Join us for traditional southern Italian food with a focus on dishes from the sun-splashed Amalfi Coast. Featuring an array of mouth-watering pasta, fresh seafood, char-grilled flatbread and more.

A photo of Deep Blue at Kitty Knight restaurant

7. Deep Blue at Kitty Knight

4.4

Awesome(312)

££££Price: Moderate

• Seafood • Chesapeake City

Booked 1 time today

Deep Blue at Kitty Knight in Galena, MD offers gorgeous views of the Sassafras River and fresh, local ingredients.

8. Pithari

4.7

Exceptional(146)

££££Price: Expensive

• Mediterranean • Middletown

Booked 17 times today

Providing fresh Mediterranean food, from our kitchen to you!

A photo of Bridges Restaurant - MD restaurant

9. Bridges Restaurant - MD

4.7

Exceptional(2106)

££££Price: Moderate

• Contemporary American • Kent Narrows

Booked 14 times today

Bridges is an OpenTable "Top 100 Scenic View Restaurant in America". Located in the heart of the Chesapeake, Bridges restaurant offers unmatched waterfront dining featuring made-to-order dishes that are prepared from scratch using the finest hand-picked ingredients. Open daily for lunch and dinner, Bridges offers an award-winning happy hour Sunday through Friday. Come enjoy the spectacular views and taste the best of the Chesapeake Bay region!

A photo of Conrad's Seafood Restaurant restaurant

10. Conrad's Seafood Restaurant

4.7

Exceptional(956)

££££Price: Moderate

• Seafood • Perry Hall

Booked 21 times today

**If you prefer to have steamed crabs please specify desired size and quantity when making your reservation so we can do our best to accommodate. Requests are not guaranteed. Please call the day of to confirm your request.**Voted Baltimore's Best crabs 10 years in a row! Available year around! Conrad's prides itself in the use of local seafood, meats, and produce as well as being True Blue certified! We're more than just a crab house, our seasonal menu prepared by Chef Lancelotta offers the ultimate Maryland seafood experience. From fresh fish, seasonal raw oysters on the half shell, fresh local soft shell crabs, or everyone's favorite Conrad's crab fries, there truly is something on the menu for everyone! Featuring our unique boat bar and awesome outdoor bar/patio!

See what locals rave about

From verified diners like you

OT
OpenTable Diner
Montana •2 reviews
5.0
Dined 2 days ago
Wonderful atmosphere, great food and incredible service!
More info
Tagliata RestaurantPrice: Expensive• Italian• Harbor East
•
4.8
KC
KolaC
Washington, D.C. Area •3 reviews
5.0
Dined 2 days ago
Made reservations for 8:45 got there around 8:30 and was seated right away. The ambiance was amazing and the food was delicious. We will be returning again.
More info
The RuxtonPrice: Very Expensive• Steakhouse• Harbor East
•
4.8
C
ChristianVIP
West Palm Beach •10 reviews
5.0
Dined 3 days ago
Super meal Neyah, thanks. You’ve got a great team. The meat loaf and pork dish were exceptional, as was the shrimp starter.
More info
The Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown
•
4.8
A
Andrew
Philadelphia County •4 reviews
5.0
Dined 6 days ago
Wonderful dinner at Osprey tonight. It was chilly and windy so we were able to sit by the fireplace. Very nice. Our meal and our server were excellent. Very enjoyable
More info
Osprey Point RestaurantPrice: Expensive• Contemporary American• Rock Hall
•
4.8
R
Rocco
Washington, D.C. Area •6 reviews
5.0
Dined 6 days ago
Everything was great, will definitely go back, our waiter Dan was fantastic. Juan the bartender makes the best drinks!!
More info
BygonePrice: Very Expensive• American• Harbor East
•
4.6

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Chestertown

Baltimore / Maryland