Bed and Breakfast and Inn in Chesapeake Bay

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Chesapeake Bay B&B
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537 Bed and Breakfast and Inn in Chesapeake Bay

Best Chesapeake Bay bed and breakfasts with breakfast included

Inn At Haven Harbour - Chesapeake Bay
8.6 4 reviews

Inn At Haven Harbour

B&B, Rock Hall
This beachfront guesthouse in Rock Hall offers direct access to the shore and is within a 15-minute walk of the Waterman's Museum, Rock Hall Harbour, and The Mainstay.
Guests can enjoy a complimentary continental breakfast, on-site dining at two restaurants, a seasonal outdoor swimming pool, and free WiFi in public areas, with business facilities also available.
Inn On Main Annapolis - Chesapeake Bay
8.2 268 reviews

Inn On Main Annapolis

B&B, Annapolis
The Inn on Main Annapolis is located just 1.2 miles from Annapolis Harbour, putting you within easy reach of the city's historic district, charming shops and restaurants. The B&B has received very good user ratings, with an excellent location rating and a very good cleanliness rating.
The rooms are all equipped with free Wi-Fi, air conditioning and flat-screen TVs, providing a comfortable stay. Guests can enjoy a delicious American breakfast every morning, relax on the terrace or dine at the Inn's restaurant, which serves American cuisine.
Magnolia House Inn - Chesapeake Bay
9.8 18 reviews

Magnolia House Inn

B&B, Hampton
Magnolia House Inn is situated in Hampton, just a short drive from attractions like Busch Gardens, Colonial Williamsburg, and the Virginia Living Museum. The inn enjoys an excellent reputation, with guests consistently praising its cleanliness, location, and overall experience.
The inn offers comfortable rooms, each with a private bathroom, air conditioning, and a flat-screen TV. Guests can enjoy a delicious breakfast, relax in the garden, and take advantage of amenities like a bar, fitness centre, and free parking.
Gramercy Mansion - Chesapeake Bay
9.7 209 reviews

Gramercy Mansion

B&B, Pikesville
Gramercy Mansion is a Tudor-style mansion located in Stevenson, Maryland, just 15 minutes from Towson, Hunt Valley, and downtown Baltimore. This charming B&B has received excellent ratings for its location, cleanliness, and overall experience.
The mansion is set on 45 acres of gardens and wooded walkways, offering a peaceful escape. Guests can enjoy a range of amenities, including a swimming pool, tennis court, spa, and restaurant, as well as a gourmet breakfast made with fresh ingredients from the property's organic farm.

Best Chesapeake Bay bed and breakfasts with a pool

Among the 537 accommodations in Chesapeake Bay, here are the 4 best b&b with a pool

Black Walnut Point Inn - Chesapeake Bay
9.0 56 reviews

Black Walnut Point Inn

B&B, Tilghman Island
This charming bed and breakfast is situated on Tilghman Island, just a short drive from the Tilghman Watermen’s Museum and within easy reach of other attractions like the Chesapeake Bay Maritime Museum and St. Michaels Museum. It has consistently received excellent reviews from guests, highlighting its beautiful location and friendly service.
The inn offers a range of comfortable rooms and features a lovely garden, barbecue grills, and a picnic area for guests to enjoy. You can also take advantage of the swimming pool, terrace, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
The Laughing King Retreat, Cedar Island Suite - Chesapeake Bay
10 1158 reviews

The Laughing King Retreat, Cedar Island Suite

B&B, Eastville
The Laughing King Retreat, an adults-only guesthouse, is situated on the Chesapeake Bay, a short drive from the Savage Neck Dunes Natural Wildlife Preserve.
This secluded waterfront farm offers a private pool, a dry sauna, a fire pit, a gazebo, a palapa, and a straw hat lending library, with the option to use the fully stocked gourmet kitchen.
Spacious Home With An Outdoor Pool, Screened Porch, Washer Dryer & Central Ac - Chesapeake Bay
No reviews

Spacious Home With An Outdoor Pool, Screened Porch, Washer Dryer & Central Ac

B&B, Highland Beach
This Bed & Breakfast is situated in Highland Beach, 8 kilometres from Annapolis Harbour and 38 kilometres from Baltimore/Washington International Airport.
This 279 square metre guesthouse offers 3 bedrooms, 3 bathrooms, accommodating up to 10 guests, and features a private outdoor swimming pool, a screened porch, air conditioning, and a fully equipped kitchen, with an in-unit washer and dryer for added convenience.
George Brooks House B&b - Chesapeake Bay
8.6 86 reviews

George Brooks House B&b

B&B, Easton
The George Brooks House B&B is located in St. Michaels, a short drive from Easton, and is just a short distance from the Chesapeake Bay Maritime Museum and the town centre. It has a very good rating for location, cleanliness, and overall user experience.
The guest house has one bedroom and one bathroom, accommodating up to two guests. Amenities include a swimming pool, jacuzzi, garden, terrace, kitchen, and free Wi-Fi, as well as a DVD library and complimentary bikes, making it ideal for a relaxing getaway.

Frequently Asked Questions about bed and breakfast in Chesapeake Bay

  • What are the must-see sights for first-time visitors on a day trip to Baie de Chesapeake?

    For a day trip to Chesapeake Bay, you should definitely visit Annapolis, the state capital of Maryland. It's a charming city with a historic waterfront and plenty of shops and restaurants. You could also take a boat trip to see the Chesapeake Bay Bridge, a stunning landmark that connects the Eastern Shore to the mainland.
  • What are the best bed and breakfasts in Chesapeake Bay?

  • In which districts of Baie de Chesapeake should you consider booking a bed and breakfast?

    If you're looking for a bed and breakfast, you can't go wrong with St. Michaels, a picturesque town on the Eastern Shore known for its beautiful architecture and waterfront views. Another great option is Easton, a historic town with a vibrant arts scene and plenty of charming shops and restaurants.
  • What are the best bed and breakfasts with a pool in Chesapeake Bay?

  • What is the typical weather in Baie de Chesapeake, and how does it affect outdoor plans?

    The Chesapeake Bay area has four distinct seasons. Summers are hot and humid, with temperatures reaching up to 32°C. Winters are mild, with average temperatures around 5°C. Spring and autumn are beautiful, with mild temperatures and plenty of sunshine. The weather can be unpredictable, so it's always a good idea to check the forecast before heading out.
  • What are the best bed and breakfasts with a jacuzzi in Chesapeake Bay?

  • What are the best cultural activities and events in and around Baie de Chesapeake?

    The Chesapeake Bay area is home to many cultural events throughout the year, including the Annapolis Maritime Museum, the Chesapeake Bay Maritime Museum, and the annual Chesapeake Bay Wine Festival. If you're interested in history, be sure to visit the historic district in Annapolis.
  • What are the best bed and breakfasts for families and kids in Chesapeake Bay?

  • Which hiking trails are recommended for exploring in and around Baie de Chesapeake?

    For hiking, I recommend the Bay Country Trail, a 160-kilometre trail that runs along the Eastern Shore of Maryland. It's a great way to experience the natural beauty of the Chesapeake Bay area. Another popular option is the Harriet Tubman Underground Railroad Byway, a scenic route that follows the path of the Underground Railroad.
  • What are the best pet friendly bed and breakfasts in Chesapeake Bay?

  • What amenities are commonly offered in bed and breakfasts in Baie de Chesapeake?

    Bed and breakfasts in the Chesapeake Bay area typically offer a variety of amenities, including a hearty breakfast, free Wi-Fi, and parking. Many also have a swimming pool, hot tub, or other outdoor amenities.
  • What are the best bed and breakfasts with parking in Chesapeake Bay?

Popular destinations

Best Chesapeake Bay bed and breakfasts with a garden

The Inn At Tacaro Estate - Chesapeake Bay
9.0 28 reviews

The Inn At Tacaro Estate

B&B, Deale
The Inn at Tacaro Estate is located in Tracys Landing, a short drive from Annapolis and Washington D.C., offering a peaceful escape from the city. This B&B has excellent user and location ratings, making it a great choice for a relaxing getaway.
The Inn at Tacaro Estate has one bedroom and one bathroom, covering 71 square metres. Guests can enjoy amenities such as a swimming pool, jacuzzi, terrace, garden, free parking, and complimentary Wi-Fi.
Solomons Victorian Inn - Chesapeake Bay
10 116 reviews

Solomons Victorian Inn

B&B, Solomons
Solomons Victorian Inn is located in Solomons, Maryland, just 1.8 kilometres from the Calvert Marine Museum and 5 kilometres from Annmarie Garden. The inn has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
This charming bed and breakfast can accommodate two guests in its single bedroom with a private bathroom. Amenities include a fully equipped kitchenette, a hot tub, a terrace, a garden, and free Wi-Fi and parking.
Bay View Studio Apartment - Chesapeake Bay
9.9 165 reviews

Bay View Studio Apartment

B&B, Annapolis
This waterfront flat is situated in Annapolis, just a 1.6km walk from the Annapolis Sailing School and Annapolis Landing Marina, and within 5km of the Bay Bridge Market Place Shopping Center and Sparrows Beach. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The apartment has one bedroom, one bathroom, and can accommodate up to four guests comfortably. The 93 square meter space features a fully equipped kitchen, a fireplace, free Wi-Fi, a washing machine, and a terrace with stunning views of the Annapolis harbour. Guests can also enjoy the on-site amenities, including a swimming pool, jacuzzi, garden, and barbecue grills.
Brampton 1860 - Chesapeake Bay
9.1 18 reviews

Brampton 1860

B&B, Chestertown
The Brampton Bed and Breakfast Inn is located on Maryland's Eastern Shore, a short distance from Chestertown's centre and Washington College, offering a peaceful escape in the beautiful Maryland countryside. The B&B has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This charming 19th-century inn can accommodate up to two guests in its single bedroom and bathroom. Enjoy a range of amenities including a spa, a terrace, a garden, and a restaurant, perfect for a relaxing and enjoyable stay.

Best Chesapeake Bay bed and breakfasts with air conditioning

Historic Madison Ave - Chesapeake Bay
8.9 25 reviews

Historic Madison Ave

B&B, Baltimore
This guesthouse in Baltimore's Historic Madison Avenue is located 2.25 kilometres from The Walters Art Museum and the Edgar Allan Poe Museum.
Offering excellent user ratings, this 1-bedroom, 1-bathroom B&B accommodates two guests and features air conditioning, free WiFi, on-site parking, a shared kitchen, a terrace, and bicycle and car rental services.
Marvels On The Creek - Chesapeake Bay
9.9 241 reviews

Marvels On The Creek

B&B, Secretary
Marvels on the Creek is a charming bed and breakfast situated just 20 miles from the Academy of the Arts and 14 miles from Federalsburg Marina, offering a tranquil escape in the heart of Secretary. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The bed and breakfast features a single bedroom and bathroom, accommodating up to two guests. Amenities include a swimming pool, jacuzzi, spa, restaurant, room service, and a garden, providing a relaxing and luxurious experience.
The Whitehaven Hotel - Chesapeake Bay
10 166 reviews

The Whitehaven Hotel

B&B, Whitehaven
This golf bed and breakfast is situated in Quantico, offering easy access to Mount Vernon Park and Cedar Hill Marina, both within 14 kilometres, and Roaring Point Park, approximately 26 kilometres away.
This family-friendly guesthouse accommodates two guests and provides complimentary cooked-to-order breakfast, free WiFi in common areas, on-site barbecue grills, a picnic area, and complimentary bicycle hire for exploring the local area, with convenient, free self-parking available.
Cozy 1br Basement Private Retreat In Downtown Baltimore - Chesapeake Bay
10 1 review

Cozy 1br Basement Private Retreat In Downtown Baltimore

B&B, Baltimore
This B&B offers a homestay experience in Downtown Baltimore, an 8-minute walk from the University of Maryland - Baltimore and within 2 kilometres of the Edgar Allan Poe Museum, the Sports Legends Museum at Camden Yards and the Inner Harbour.
This accommodation provides one bedroom and one bathroom for up to three guests, with complimentary WiFi, air conditioning, parking, a shared kitchen and lounge, and an outdoor seating area.
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