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Restaurants near Historic Inns of Annapolis

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414 restaurants available nearby

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A photo of The Choptank - Annapolis restaurant
1. The Choptank - Annapolis
4.6
Exceptional(1943)
$$$$
• Seafood • Annapolis
Booked 142 times today
Local Chesapeake Seafood and Crabhouse featuring live entertainment, craft cocktails, carefully curated wine list, and the best scenic view of the Chesapeake in the region!
A photo of Osteria 177 restaurant
2. Osteria 177
5.0
Exceptional(3826)
$$$$
• Italian • Annapolis
Booked 35 times today
Osteria 177 is the ultimate expression of an Italian tavern where the main attraction is imported delicacies of one-of-a-kind food and wine. Adorned by barreled wine, an Osteria would never lack the sought out local specialties, spices, cheeses, fish or meats. It was here that many people tried to alleviate life's stresses by numbering themselves with good food, good wine, and good company. The owner/chef of the Osteria would take the utmost pride in stocking these praised elements as the basis for mouthwatering meals, a delicious dance-for-all of the five senses. This is the basis for Osteria 177.
A photo of Acqua al 2 - Annapolis restaurant
3. Acqua al 2 - Annapolis
4.7
Exceptional(1089)
$$$$
• Italian • Annapolis
Booked 30 times today
Located in the heart of Annapolis, Acqua al 2 offers an authentic Tuscan dining experience. Featuring a wide array of vegetarian pasta, hand-carved steaks, and fresh seafood, as well as an extensive Italian wine list, Acqua is perfect for a celebratory dinner, an intimate date night, or a low key get-together with friends. Please note: A Labor of Love fee of 3% is added to all checks to support employee benefits.
A photo of Cafe Normandie restaurant
4. Cafe Normandie
4.4
Awesome(2795)
$$$$
• French • Annapolis
Booked 9 times today
Consistently voted "Most Romantic" restaurant, Cafe Normandie combines French cuisine with local Maryland specialities. A family business, we have been located in Historic Annapolis for 35 years.
A photo of Rams Head Tavern - Annapolis restaurant
5. Rams Head Tavern - Annapolis
4.7
Exceptional(1830)
$$$$
• American • Annapolis
Booked 23 times today
For over 30 years, Rams Head has been an award-winning favorite serving creative tavern fare. Rams Head offers an outstanding happy hour, a legendary beer selection, and extraordinary live music 7 nights a week. Whether in one of the cozy dining rooms, the historic pub, or on the Wisteria-covered patio, you'll see why so many Annapolitans consider Rams Head their second home. .We do not accept reservations for outdoor dining. Have tickets to a show at Rams Head On Stage? If taking advantage of our FREE Premium On Stage Experience, please make note in the 'special request' section while making your reservation.
A photo of Fox's Den restaurant
6. Fox's Den
4.7
Exceptional(362)
$$$$
• Gastro Pub • Annapolis
Booked 4 times today
An american craft Gastropub concentrating on local and small batch beers, whiskey, spirits and hand crafted cocktails along with a brick oven menu with Wood Fired Pizza, shareable items, and small plates. *Please note for online wait listed reservations do have a 5-10 min time frame to arrive for your reservation to be sat*
A photo of Luna Blu - Annapolis restaurant
7. Luna Blu - Annapolis
4.9
Exceptional(2650)
$$$$
• Italian • Annapolis
Booked 27 times today
We opened in 2001 on the new up & coming hot spot of Inner West Street. We have grown into a neighborhood favorite among locals & tourists. Our cozy dining room with murals of the Amafi Coast is the perfect place for a date night or for making memories with friends & family. Offering innovative Italian fare prepared with a personal touch & the freshest local ingredients. Menu items are prepared fresh to order, which allows us to be very accommodating to food allergies. Many options for vegans, pescatarians, and gluten-free diners.Wednesday & Saturday from May - Sept on West Street's 1st block, we hold Dinner Under the Stars. All of the restaurants put tables & chairs under a light canopy, there is live music and dancing. We offer a 4-course special nightly, 1/2 priced bottles of wine every Wednesday, Pizza & Wine pairing Tuesday & Thursday nights & and bi-weekly wine dinners.View our events & specials www.lunabluofannapolis.com Thanks for supporting local business!
A photo of Harold Black - Annapolis restaurant
8. Harold Black - Annapolis
4.6
Exceptional(90)
$$$$
• Italian • Annapolis
Booked 1 time today
Given that Harlod Black is a cocktail bar, the age requirement for entering is 21.Harold Black is a warm, intimate bar that is quiet enough to hear your conversation yet lively enough to keep you talking. A list of house cocktails gives you a range of options; additionally, the bartenders are ready to work their magic if you have something else in mind. Harold Black serves the same menu as Acqua with a couple of pub-style additions. Please be aware of a few house rules: 1. We look forward to having you join us and are happy to hold your table for up to fifteen minutes. 2. Your booking reserves your seats for 2 hours. 3. Due to our small size we cannot guarantee booth seating. 4. Our maximum party size is six people, no exceptions, and unfortunately we cannot book multiple tables for one group. To buy out Harold Black for a private event or book our private dining room, please email events@haroldblack.com. A Labor of Love fee of 3% is added to all checks to support employee benefits.
A photo of Iron Rooster restaurant
9. Iron Rooster
4.7
Exceptional(997)
$$$$
• Breakfast • Annapolis
Booked 9 times today
Whether you're looking for breakfast all day, lunch, supper or drinks, at Iron Rooster you'll find a new twist on traditional comfort food, legendary hospitality, and a real sense of community. Join us every day for breakfast, lunch, supper and late-night drinks. Whenever you're here, you'll enjoy delicious food, a cold drink, and an extra helping of hospitality.
A photo of Parley Room restaurant
10. Parley Room
4.8
Exceptional(14)
$$$$
• American • Annapolis
Booked 1 time today
Pre-Prohibition era style cocktail bar. Located in historic downtown Annapolis next to State Capital Building inside the Capital Hotel Annapolis. Great patio for dining or lounging with cocktails. Fine dining level food with everyday prices and atmosphere. Parley Room offers classic and modern cocktails, in a classic cocktail bar atmosphere. For the last two years has won awards for best cocktail bar in the city and best cocktails. Parley Room is Fresh and Awesome, a must have experience in Annapolis.

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Dining near Historic Inns of Annapolis at a glance

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Most popular restaurant

popular restaurant

Osteria 177

5

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Discover local gems

Exceptional reviews

Most popular cuisine

popular cuisine

Seafood

Average check amount

$30 and under

See what locals rave about

From verified diners like you
From verified diners like you
  • JoAnnGold
    Greater Boston •7 reviews
    4.0
    Dined 2 days ago
    Unbelievable meal AGAIN! My favorite in Crab town- lemon dessert is over the moon! Halibut dish divine- always top notch dinning from start to finish!
    More info
    Acqua al 2 - Annapolis$$$$• Italian• Annapolis
    •
    4.7
  • Dennis
    Baltimore / Maryland •14 reviews
    5.0
    Dined 2 days ago
    The wine and food were delicious. Always outstanding, and the size of the escargot was amazing.
    More info
    Cafe Normandie$$$$• French• Annapolis
    •
    4.4
  • TerenceGold
    Washington, D.C. Area •27 reviews
    4.0
    Dined 2 days ago
    Smash Burger is excellent. Go on Monday for a BOGO
    More info
    Rams Head Tavern - Annapolis$$$$• American• Annapolis
    •
    4.7
  • Camille
    Baltimore / Maryland •1 review
    5.0
    Dined 3 days ago
    I had a reservation made for my mom and I on Mother's Day and it was the best! The location is beautiful, set on the water in Annapolis, and the place was clean and airy (I loved the spacious venue with all the open windows, we were able to enjoy the nice day). Food was amazing, our server David (or Daniel? can't remember) made really good recommendations and was super kind and attentive. Many restaurants can have a good venue and good food but the only thing that will get me to write a good review is the good service, I can't tell you enough how thankful I am for our server and the manager of the place, Lynn. They made sure my mom and I were taken care of, and were satisfied with our experience. Highly recommend this place! :)
    More info
    The Choptank - Annapolis$$$$• Seafood• Annapolis
    •
    4.6
  • Deborah
    Baltimore / Maryland •44 reviews
    5.0
    Dined on May 5, 2026
    Ours was a party of two celebrating a birthday. Our server was outstanding and answered the questions we had about their outstanding menu. So many choices and categories of food and wine, it was hard to choose. The sea bass was one of the best I ever had, and the bottle of Chianti we ordered was beautiful. This is an awesome restaurant. If you’ve never been, you’ve got to check it out!
    More info
    Osteria 177$$$$• Italian• Annapolis
    •
    5

Discover best restaurants near Historic Inns of Annapolis

Discover the charm of the Historic Inns of Annapolis, a delightful collection of quaint accommodations steeped in history, perfect for exploring the vibrant city of Annapolis. Where to Eat Near Historic Inns of Annapolis? Just steps away, you’ll find an array of dining options to satisfy any culinary craving. The area boasts cozy taverns offering hearty American fare, inviting seafood spots showcasing the best of the Chesapeake, and elegant Italian eateries serving fresh pastas and exquisite wines. Enjoy casual dining with lively atmospheres and friendly service, making it easy to unwind after a day of exploration. Whether you’re in the mood for fresh seafood, comforting Italian dishes, or classic American pub grub, the dining scene near the Historic Inns offers something for everyone.

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