Bed and Breakfast in Chesapeake Bay

280 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Chesapeake Bay bed and breakfast
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

280 Bed and Breakfasts in Chesapeake Bay

Best Chesapeake Bay bed and breakfasts with breakfast included

Solomons Victorian Inn - Chesapeake Bay
9.9 108 reviews
Chesapeake Bay
01/10 – 05/10
NZ$1064/nighttotal: NZ$4256 (4 )

Solomons Victorian Inn

2 3
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.
Carib Comfort B And B - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
NZ$418/nighttotal: NZ$2926 (7 )

Carib Comfort B And B

1 2
B&B , Brock Hall
This Brock Hall guest house is situated in Upper Marlboro, offering garden views and located 24.1 kilometres from the U.S. Capitol and 16.1 kilometres from Washington Union Station.
This B&B provides one bedroom and one bathroom for up to two guests, featuring air conditioning, complimentary Wi-Fi, on-site parking, a garden, a bar, and a daily continental breakfast.
The Inn At Tacaro Estate - Chesapeake Bay
9.0 30 reviews
Chesapeake Bay
29/08 – 05/09
NZ$941/nighttotal: NZ$6587 (7 )

The Inn At Tacaro Estate

1 2
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.
Rachael's Dowry Bed And Breakfast - Chesapeake Bay
9.2 28 reviews
Chesapeake Bay
29/08 – 05/09
NZ$574/nighttotal: NZ$4018 (7 )

Rachael's Dowry Bed And Breakfast

1 2
B&B , Baltimore
Rachael's Dowry Bed and Breakfast is conveniently located in Baltimore city centre, just a short walk from Camden Yards and the Inner Harbor. It has received excellent ratings for its cleanliness, location and overall user experience.
The guest house offers a charming 18th-century setting with modern amenities, including a shared kitchenette, a tranquil garden and a courtyard. Guests can enjoy a daily organic breakfast and explore the city's attractions with ease.

Best Chesapeake Bay bed and breakfasts with a pool

Among the 280 accommodations in Chesapeake Bay, here are the 4 best B&B with a pool

Inn At Huntingfield Creek - Chesapeake Bay
9.7 132 reviews
Chesapeake Bay
29/08 – 05/09
NZ$613/nighttotal: NZ$4291 (7 )

Inn At Huntingfield Creek

1 2
B&B , Rock Hall
The Inn at Huntingfield Creek is located in Rock Hall, Maryland, just 92 miles from Baltimore and 63 miles from Annapolis, making it a convenient base for exploring the Chesapeake Bay. The Inn has consistently received excellent ratings for its cleanliness, location, and overall experience.
The guest house offers a comfortable and spacious room with a private bathroom. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax in the shared lounge, or take advantage of the free WiFi. A full English/Irish breakfast is provided each morning, and the Inn also offers cycling and canoeing opportunities for those wanting to explore the surrounding area.
Gramercy Mansion - Chesapeake Bay
9.7 205 reviews
Chesapeake Bay
23/08 – 28/08
NZ$345/nighttotal: NZ$1725 (5 )

Gramercy Mansion

1 2
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.
The Laughing King Retreat, Cedar Island Suite - Chesapeake Bay
10 1117 reviews
Chesapeake Bay
23/08 – 28/08
NZ$436/nighttotal: NZ$2180 (5 )

The Laughing King Retreat, Cedar Island Suite

1 2
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.
Splendid Home With Private Pool, Fire Pit, Several Decks & Balconies - Chesapeake Bay
Chesapeake Bay
23/08 – 28/08
NZ$1003/nighttotal: NZ$5015 (5 )

Splendid Home With Private Pool, Fire Pit, Several Decks & Balconies

4 2
B&B , Riva
This Annapolis guesthouse is located 14 kilometres from Annapolis Harbour, with attractions such as the Sports Legends Museum at Camden Yards and the Power Plant situated approximately 42 to 43 kilometres away.
This 476 square metre Bed and Breakfast offers accommodation for up to 23 guests, featuring air conditioning, a swimming pool, a garden, a children's playground, and a kitchen equipped with a fridge, microwave oven, and dishwasher, all within 27 kilometres of Baltimore - Washington International Airport.

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 can't go wrong with a visit to Annapolis, the state capital of Maryland. It's a charming historic city with lots of beautiful architecture, including the US Naval Academy. You can also enjoy a scenic boat trip on the bay itself, taking in the views of the water and the surrounding landscape.
  • 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 should consider the Eastern Shore of Maryland. There are lots of charming towns like St. Michaels, Easton, and Oxford with lots of lovely B&Bs. You'll find a more relaxed atmosphere than you get on the western shore, which tends to be more urban.
  • What are the best bed and breakfasts with a pool in Chesapeake Bay?

  • What dining options are recommended for solo travelers staying at bed and breakfasts in Baie de Chesapeake?

    Many bed and breakfasts offer a delicious breakfast, but for dinner, you can try the Chesapeake Inn in Grasonville for fresh seafood. It's a popular spot with locals and visitors alike, and they often have live music on the weekends.
  • 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 Maritime Museum in St. Michaels is a great place to learn about the history of the bay and its maritime traditions. You can also visit the annual Chesapeake Bay Wine Festival, which takes place in September and features wines from local vineyards.
  • 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, the Assateague Island National Seashore is a great option. You can hike along the beach, through the dunes, and through the maritime forest. There's also the Blackwater National Wildlife Refuge, which has a variety of trails for different levels of hikers.
  • 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 Chesapeake Bay typically offer a range of amenities, including a hearty breakfast, comfortable rooms, and often a shared living area. Some B&Bs also have swimming pools, hot tubs, and gardens. You can find some that offer a more luxurious experience, with amenities like fireplaces and private balconies.
  • What are the best bed and breakfasts with parking in Chesapeake Bay?

Destinations nearby

Best Chesapeake Bay bed and breakfasts with a garden

Waterfront On St. Leonard Creek At Fort Hill - Chesapeake Bay
10 101 reviews
Chesapeake Bay
01/10 – 05/10
NZ$324/nighttotal: NZ$1296 (4 )

Waterfront On St. Leonard Creek At Fort Hill

1 3
B&B , Long Beach
This waterfront apartment is situated in Southern Maryland, just 80 kilometers from Washington, D.C., offering a peaceful retreat away from the city bustle. Guests have consistently rated it excellent for location, cleanliness, and overall experience. The apartment is a split-level home with a private entrance and dedicated outdoor space, comfortably accommodating up to five guests. It comes equipped with a kitchenette, air conditioning, a large-screen TV, and access to a private pier, kayaks, and a fire pit, making it ideal for exploring the surrounding waterways and enjoying outdoor activities.
The Inn At Tacaro Estate - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
NZ$880/nighttotal: NZ$6160 (7 )

The Inn At Tacaro Estate

1 2
B&B , Deale
The Inn at Tacaro Estate, a guest house in Tracys Landing, is situated approximately 3 kilometres from Deale's town centre.
This pet-friendly lodging offers a swimming pool, restaurant, free Wi-Fi, and parking, sleeping up to two guests with one bathroom.
Marvels On The Creek - Chesapeake Bay
9.8 359 reviews
Chesapeake Bay
01/10 – 05/10
NZ$688/nighttotal: NZ$2752 (4 )

Marvels On The Creek

2 3
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.
Wades Point Inn On The Bay - Chesapeake Bay
9.6 143 reviews
Chesapeake Bay
01/10 – 05/10
NZ$684/nighttotal: NZ$2736 (4 )

Wades Point Inn On The Bay

1 3
B&B , Tilghman Island
Wades Point Inn on the Bay is situated in Saint Michaels, Maryland, just a short drive from the Academy of the Arts and a convenient distance from Salisbury-Ocean City Wicomico Regional Airport. This charming bed and breakfast has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The inn offers a single bedroom with a range of amenities, including a fridge, microwave, air conditioning, a terrace, a garden, and room service. Guests can enjoy a waterfront location with stunning views, relax by the outdoor fireplace, and take advantage of complimentary bikes to explore the surrounding area.

Best Chesapeake Bay bed and breakfasts with air conditioning

Sandaway Suites & Beach Waterfront Hotel Oxford Md - Chesapeake Bay
9.9 46 reviews
Chesapeake Bay
23/08 – 28/08
NZ$416/nighttotal: NZ$2080 (5 )

Sandaway Suites & Beach Waterfront Hotel Oxford Md

1 2
B&B , Oxford
Sandaway Suites & Beach, a guesthouse in Oxford, Maryland's historic district, offers easy access to restaurants and shops, and is conveniently located for day trips to St. Michaels, Easton, and Cambridge.
This adults-only, pet-free, non-smoking establishment provides a guest house with one bedroom, one bathroom, sleeping up to two guests, and features a private beach, kayak and bike rentals, plus Tesla and electric car charging stations.
River Guest Suite W/ Pool, Beach, Private Boatslip - Chesapeake Bay
9.9 33 reviews
Chesapeake Bay
30/07 – 05/08
NZ$658/nighttotal: NZ$3948 (6 )

River Guest Suite W/ Pool, Beach, Private Boatslip

1 6
B&B , Grasonville
This charming bed and breakfast is located in Grasonville, offering stunning riverfront views and unforgettable sunsets. The property is highly rated, with excellent reviews for its cleanliness, location and overall experience.
The accommodation features a single bedroom and bathroom, ideal for couples seeking a peaceful retreat. Guests can enjoy a range of amenities, including a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden and parking.
Wilson House Bed & Breakfast - Chesapeake Bay
9.6 151 reviews
Chesapeake Bay
29/08 – 05/09
NZ$253/nighttotal: NZ$1771 (7 )

Wilson House Bed & Breakfast

1 2
B&B , Baltimore
This Baltimore guesthouse is conveniently located less than 1.6km from the Maryland Institute College of Art, and within a 10-minute drive of Baltimore's city centre and Inner Harbour.
Offering one bedroom and one bathroom, this Baltimore B&B provides complimentary full breakfast, free Wi-Fi, evening wine and cheese, and parking, plus uniquely decorated rooms with antiques.
1896 Historic Bed & Breakfast Mansion With A General Store - Chesapeake Bay
9.8 8 reviews
Chesapeake Bay
30/07 – 05/08
NZ$1375/nighttotal: NZ$8250 (6 )

1896 Historic Bed & Breakfast Mansion With A General Store

6 6
B&B , Newport News
The Historic Boxwood Inn is located in the Lee Hall area of North Newport News, just 16 kilometres from Busch Gardens Williamsburg and 20 kilometres from Colonial Williamsburg. The inn is set in a quiet residential area, with easy access to the main attractions of the region.
The inn is a 19th-century property with five bedrooms and four bathrooms, providing accommodation for up to 12 guests. It features a range of amenities including a terrace, garden, air conditioning, and free Wi-Fi. The inn also boasts a variety of room options, including a Grand Suite, a Family Suite, a Train Suite, and a Grooms Room.
©2026 cozycozy.com