Best Hotels on Chesapeake Bay

Located on Maryland’s Eastern Shore, this colonial mansion features a full-service spa, various dining options, and panoramic views of the Chesapeake Bay. The Offshore Sailing School is on-site. Cable TV, free WiFi access, and an iPod dock are featured in every guest room at Inn at Perry Cabin. Decorated in crisp, bright colors and dark wood furnishings, the rooms also have an private bathroom. Guests can relax on the lounge chairs by the outdoor pool or use the fitness center where yoga classes are available. Guests can also stroll through the lush flower gardens and greenhouse at the Inn at Perry Cabin. Overlooking the water, Stars serves breakfast, lunch, and dinner. Enjoy a cocktail by the fireplace at Purser's Pub. Various shops and antique stores in St. Michael’s town center are within 10 minutes’ walk.

- "Beautiful views with amazing food" - "Top hotel you worh a detour." - "The stay was a needed getaway and was absolutely perfect." - "it was a very enjoyable weekend with family" - "Wonderful hotel experience" - "Relaxing, quick one night with a best friend." - "Perfect weather for a wonderful stay at this beautiful resort despite astronomical prices." - "Go at least once!" - "Beautiful getaway spot with top-notch service and amenities, and only minor blips in room conveniences."

Spread across three historic buildings in the Annapolis city center, this hotel offers free WiFi throughout the property. The United States Naval Academy is 5 minutes' walk away, while the Maryland State House is just 328 feet from the property. A 42-inch flat-screen TV and plush bedding are offered in each uniquely decorated room at Historic Inns of Annapolis. All rooms feature warm decor and certain rooms come with a work desk or seating area. An private bathroom is provided and comes with free toiletries. A 24-hour reception is also provided along with fax and photocopying services. Valet parking is offered at an additional fee. A variety of dining and shopping options are within walking distance. St. John's College is just 4 minutes' walk from the hotel.

- "This will be the first of many stays!" - "Great location! Walking distance to places of interest. Very historic and quaint." - "Comfy, Cozy, and centrally located for easy walking access to most of the historic area of Annapolis" - "Nice get away." - "Wonderful historic hotel in fantastic location" - "Wonderful but brief stay. Close to downtown Annapolis and the Naval Academy." - "Perfect for a weekend getaway" - "Excellent"

Facing the beachfront, Sandaway Suites & Beach offers 3-star accommodations in Oxford and features a garden, private beach area and terrace. Certain rooms at the property include a balcony with a sea view. The hotel will provide guests with air-conditioned rooms offering a desk, a coffee machine, a fridge, a microwave, a safety deposit box, a flat-screen TV and a private bathroom with a shower. Guest rooms have a closet. An à la carte, continental or vegetarian breakfast is available at the property. Bike rental and car rental are available at Sandaway Suites & Beach and the area is popular for fishing and cycling. Academy Of The Arts is 10 miles from the accommodation. Salisbury-Ocean City Wicomico Regional Airport is 54 miles away.

- "It was a beautiful stay on a beautiful property." - "Exactly what we both needed. Exceptionally fun to watch the sailing lessons on Thursday afternoon!!!" - "Go to relax and see an amazing European beech tree." - "Comfortable, peaceful, resort on Chesapeake Bay. A gem and so unique." - "“I recently stayed at Sandaway Suites in Oxford, Maryland, and it was an absolutely unforgettable experience. If you’re" - "We felt very relaxed and well taken care of at Sandaway."

Located in Saint Michaels, Wades Point Inn on the Bay provides free WiFi, and guests can enjoy free bikes, a terrace and water sports facilities. After a day of hiking, fishing or cycling, guests can relax in the garden or in the shared lounge area. Academy of the Arts is 26 km from the bed and breakfast. The nearest airport is Salisbury-Ocean City Wicomico Regional Airport, 110 km from Wades Point Inn on the Bay.

Offering a garden, Inn at Warner Hall features accommodations in Gloucester. Each accommodation at the 5-star bed and breakfast has garden views, and guests can enjoy access to free bikes and massage services. The bed and breakfast offers rooms with air conditioning, free private parking, and free Wifi. At the bed and breakfast, each unit comes with a desk, a flat-screen TV, a private bathroom, bed linen, and towels. At the bed and breakfast, some units are allergy-free. Guests at the bed and breakfast can enjoy an American breakfast. Guests may relax in the on-site bar or lounge, while packed lunches are also available upon request. Guests at Inn at Warner Hall can enjoy cycling nearby, or make the most of the sun terrace. Busch Gardens & Water Country is 22 miles from the accommodation, while Colonial Williamsburg is 28 miles away. Newport News/Williamsburg International Airport is 21 miles from the property.

- "It was great"

Where a bayside cool retreat awaits: a rebirth of an 1898 original boarding house where watermen ran the docks and crabs were piled high on picnic tables. The Wylder Hotel Tilghman Island, located on a 3-mile island on the Chesapeake Bay, is a remake of an iconic property. It is an all-season escape that honors hardworking fisherman of yesteryear in an irreverent manner. This waterfront hotel makes you feel right at home with its welcoming vibe and great offerings: Tickler’s Crab Shack & Restaurant, Bar Mumbo, a private marina with 25 boat slips, charter fishing trips, and plenty of fun-filled activities. Wylder Hotel Tilghman Island is an awesome location for overnight guests, locals, as well as private gatherings and celebrations. A short drive from Baltimore, Washington D.C. and Philadelphia, Tilghman Island is a relaxed, yet exciting Eastern Shore escape. Drive through St. Michael’s, past the farmland, corn stalks and pumpkin patches, and over the drawbridge across Knapp’s Narrow, and you’ll be on our 3-mile stretch of salty paradise. From charter fishing, to sailing and kayaking, Tilghman Island life is built around the Chesapeake Bay and its bounty of pleasures. Crack your blue crab in the glow of our super-sized sunset, wash it down with a cold one and give yourself a high five from us here at Tilghman Island.

- "Quiet and restful ." - "Rest and relaxation accomplished" - "Relaxing" - "The Wyler Hotel is a unique property, beautifully situated along the Chesapeake Bay, with an excellent restaurant and ma" - "Relaxing getaway." - "I recommend The Wylder. GREAT FOOD." - "Food was excellent! Room was ok but would have preferred a comfortable chair to relax." - "Nice stay, just a few things to iron out" - "Had a great time would return again"

Inn at Osprey Point features free bikes, seasonal outdoor swimming pool, a garden and restaurant in Rock Hall. With a bar, the property also has barbecue facilities. There is free private parking and the property provides paid airport shuttle service. Complete with a private bathroom equipped with a shower and free toiletries, all guest rooms at the inn have a flat-screen TV and air conditioning, and selected rooms will provide you with a balcony. Inn at Osprey Point has a playground. Guests at the accommodation will be able to enjoy activities in and around Rock Hall, like cycling. New Castle Airport is 60 miles away.

- "Will be making a return trip !" - "Charming and romantic place for a weekend getaway!" - "Great stay" - "Peaceful stay in nature"

The Hermitage Inn and Taphouse is offering accommodations in Petersburg. The hotel provides both free WiFi and free private parking. Guest rooms are equipped with air conditioning, a flat-screen TV with cable channels, a fridge, a coffee machine, a shower, free toiletries and a desk. Selected rooms come with a kitchenette with a microwave. Guest rooms include a private bathroom, a hairdryer and bed linen. The hotel can conveniently provide information at the reception to help guests to get around the area. The nearest airport is Shenandoah Valley Regional Airport, 77 miles from The Hermitage Inn and Taphouse.

- "King studio was nice" - "Great!" - "Great room. Great staff. Would definitely stay again. :-)" - "Great experience and friendly staff !" - "Can highly recommend" - "Overall I will now only stay here when traveling to that part of WV" - "Great rooms and staff but restaurant closed" - "Underwhelming and way over-priced."

Located in Onancock and within 21 miles of Mid-Atlantic Regional Spaceport, The Charlotte Hotel & Restaurant has a bar, non-smoking rooms, and free WiFi. At the hotel, rooms are equipped with air conditioning and a flat-screen TV. Guests at The Charlotte Hotel & Restaurant can enjoy a Full English/Irish breakfast. At the accommodation you'll find a restaurant serving American cuisine. Vegetarian and gluten-free options can also be requested. Salisbury-Ocean City Wicomico Regional Airport is 59 miles from the property.

- "Went for art show. Walked everywhere and parked out front of the local. Small town charm" - "Will come back. Great service and food. only wish is for flat pillows , which i prefer." - "It was short but sweet" - "Unusual experience."

Featuring quiet street views, Hornsby House Inn in Yorktown offers accommodations, a terrace, and a bar. This property offers access to a patio, free private parking, and free Wifi. The property features barbecue facilities and outdoor furniture. All units at the bed and breakfast come with air conditioning, a seating area, a flat-screen TV with streaming services, a kitchen, a dining area, and a private bathroom with a hair dryer, a shower, and free toiletries. A dishwasher, an oven, and microwave are also available, as well as a coffee machine. At the bed and breakfast, each unit includes bed linen and towels. Buffet and à la carte breakfast options with warm dishes, pancakes, and fruit are available. Guests at the bed and breakfast can enjoy fishing nearby, or make the most of the garden. Yorktown Beach is a 3-minute walk from Hornsby House Inn, while Busch Gardens & Water Country is 12 miles from the property. Newport News/Williamsburg International Airport is 8.1 miles away.

- "I encourage anyone to stay there." - "Booking our stay was easy on line. Reviews were helpful and informative." - "We totally enjoyed our stay and hope to return next year!" - "Thanks!"

This hotel, 0.5 miles from the Maryland State House, offers a fitness center and free WiFi throughout the hotel. Lavish guestrooms feature luxurious marble bathrooms with bathroom amenities including a bathrobe. Cable TV and a work desk are featured in all spacious guestrooms. For in-room dining, room service is provided by Annapolis Waterfront Hotel while tea and coffee making facilities are also offered. There is an in-room Strarbucks® coffee maker. Annapolis Waterfront Hotel's fitness center provides free weights and cardiovascular equipment. Private parking is offered on site. Annapolis Mall is 5.5 miles away. Free newspapers are provided as well. Pusser’s Caribbean Grille serves gourmet meals for breakfast, lunch and dinner.

- "Beautiful room, perfect view, perfect stay." - "it was great" - "Lovely" - "We had a great experience here. We will certainly come back." - "Gorgeous room and view." - "Gorgeous views and weather" - "since I know that I will be returning, that says everything to me." - "Convenience to main part of town" - "We had a magnificane time in Annapolis and had a stroll down memory lane!" - "Very good" - "Great trip to celebrate our wedding anniversary at a perfect location."

Located in Stevensville, 17 miles from Annapolis Harbor, The Inn at Chesapeake Bay Beach Club provides accommodations with a seasonal outdoor swimming pool, free private parking, a fitness center and a garden. With a shared lounge, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. Guests can enjoy American dishes at the restaurant or have a drink at the bar. All guest rooms in the hotel are equipped with a flat-screen TV. Every room is equipped with a safety deposit box, while selected rooms include a balcony. Guest rooms will provide guests with a desk and a coffee machine. The Inn at Chesapeake Bay Beach Club has a terrace. The accommodation can conveniently provide information at the reception to help guests to get around the area. Baltimore - Washington International Airport is 27 miles away.

- "Too short but lovely walk at sunset because of location" - "Relaxing and convenient" - "Wedding Venue was gorgeous hotel convenient and high end." - "Very nice" - "great!" - "It was a positive stay and I would recommend to others" - "Nice nearby , inclusive , get-a-way for couples and friends."

Featuring a modern restaurant and guest rooms with free WiFi, this downtown Annapolis hotel is less than 1 mi from the United States Naval Academy and Navy-Marine Corps Memorial Stadium. The Graduate by Hilton Annapolis offers guest rooms with 47-inch flat-screen Smart TVs. A refrigerator is included At Trophy Room, guests will find a casual neighborhood restaurant and bar,serving classic American dishes with a youthful spin. Cocktails, beer, and wine are also available. Guests of the Graduate by Hilton Annapolis are welcome to enjoy the free fitness center. The Graduate by Hilton Annapolis is a 2-minute drive from the Maryland State Capitol and less than 1 mi from St. John’s College.

- "Excellent location with exceptionally comfortable rooms" - "Really nice getaway!" - "A memorable trip made better with a stay at The Graduate!" - "We LOVED our stay at the Graduate in every way! Feels like home, but better!" - "Excellent" - "Excellent property" - "They treat me like I matter every time I check in" - "We came to town for a short visit loved the city and were able to walk everywhere we went." - "Great experience! We’ll come back!"

Located in Easton, 1312 feet from Academy of the Arts, Hummingbird Inn features air-conditioned rooms with free WiFi throughout the property. Free private parking is available on site. Certain rooms have a private bathroom with a spa bath, while others have free toiletries and a hairdryer. Some units feature a seating area where you can relax. A flat-screen TV with cable channels is provided. There is luggage storage space at the property. The bed and breakfast also offers free use of bicycles. The nearest airport is Baltimore - Washington International Airport, 43 mi from Hummingbird Inn.

- "Playing cards in the turret, lovely Xmas decorations, great staff- a perfect vacation with friends!" - "Excellent Inn in Great Location" - "Loved this getraway!" - "Wonderful classic getaway with really lovely people. A must stay in Easton" - "Wonderful Relaxing Birthday Stay" - "Can’t wait to return!" - "Great experience" - "Terrific time in a beautiful setting, friendly and super staff, and wonderful experience."

Inn at Huntingfield Creek features air-conditioned rooms in Rock Hall. Boasting a shared lounge, this property also provides guests with a seasonal outdoor pool. Free WiFi is at guests' disposal. At the bed and breakfast, the rooms include a desk. All rooms come with a private bathroom with a shower. All guest rooms come with a seating area. A Full English/Irish breakfast is available each morning at the property. Inn at Huntingfield Creek offers a terrace. A variety of popular activities are available in the area around the property, including cycling and canoeing. Baltimore is 92 mi from the accommodations, while Annapolis is 63 mi away. The nearest airport is Baltimore - Washington International Airport, 84 mi from Inn at Huntingfield Creek.

- "Lovely stop on the Chesapeake Bay on route to Washington D.C."

Featuring complimentary WiFi, The Oaks Waterfront Hotel offers accommodations in Saint Michaels. Rooms come with a flat-screen TV. Every room is equipped with a private bathroom. For your comfort, you will find bathrobes, complimentary toiletries and a hairdryer. You will find a shared lounge and a seasonal swimming pool at the property. Complimentary use of bicycles is available at this inn and the area is popular for canoeing. Annapolis is 24 mi from The Oaks Waterfront Hotel, while Cambridge is 13 mi away. Baltimore - Washington International Airport is 40 mi from the property.

- "The Oaks is a beautiful hotel. The decor is exceptional. The staff was very professional and friendl" - "A beautiful relaxing stay at a lovely, friendly place." - "We will definitely be back!" - "Top notch service and place from start to finish" - "Perfect."

Swanendele Inn offers air-conditioned accommodations in Ridge. This beachfront property offers access to free Wifi and free private parking. The accommodation features an elevator, full-day security, and luggage storage for guests. Guests can stay warm with a fireplace in every unit. There's a private bathroom with walk-in shower in every unit, along with bathrobes, a hair dryer, and free toiletries. At the bed and breakfast, each unit has bed linen and towels. A selection of options including warm dishes, local specialities, and fresh pastries are available for the American breakfast. There is a coffee shop, and packed lunches are also available. Guests at the bed and breakfast can enjoy cycling and hiking nearby, or make the most of the sun terrace. Clayton Marina is 4 miles from Swanendele Inn, while St. Mary's College of Maryland is 8.7 miles away. Ronald Reagan Washington National Airport is 78 miles from the property, and the property offers a paid airport shuttle service.

- "Perfect couples retreat" - "Fabulous and would recommend very highly" - "A most amazing hidden treasure!" - "Excellent stay! We will definitely return and tell our friends!" - "The Swandele was a delightful experience, a private location, with peaceful and beautiful grounds." - "A peaceful rest" - "Best place to come to relax and recharge!" - "Such a beautiful special place. Would return anytime!" - "10/10 would recommend. I want to go back."

Located on Maryland’s scenic Eastern Shore, this historic Easton accommodations features an on-site restaurant and bar. A variety of art galleries and shops are within 5 minutes’ walk. Each individually decorated guest room at The Tidewater Inn features a flat-screen cable TV and free Wi-Fi access. They offer plush bedding and an private bathroom. Specializing in fresh Chesapeake Bay seafood dishes, Hunter’s Tavern serves breakfast, lunch, and dinner in an intimate atmosphere. The Tidewater offers on-site parking, as well as a library for relaxing. Guests have access to the nearby recreation center. The town of St. Michaels is 10 miles from the inn. Golfing at The Easton Club is just 2 miles away.

- "A beautiful quite relaxing place" - "Loved the fact that the Inn was old and was situated so that much was within walking distance." - "It was a nice hotel for one night while we were in the area to have hard shells." - "Enjoyed our midweek stay in this charming inn right in the center of Easton’s historic district."