Bed and breakfast in Chesapeake Bay

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Chesapeake Bay bed and breakfast
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280 Bed and Breakfasts and Inn in Chesapeake Bay

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking - Chesapeake Bay
Chesapeake Bay
27/06 – 04/07
A$1032/nighttotal: A$7224 (7 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 3
B&B, Annapolis
This historic downtown Annapolis townhouse is situated just over 1.7 kilometres from Annapolis Harbour, offering convenient access to the city's waterfront.
This bed and breakfast provides accommodation for up to 11 guests across 2 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, on-site spa, free private parking, and a children's playground.
Adventure Annapolis - Chesapeake Bay
Chesapeake Bay
02/07 – 05/07
A$1080/nighttotal: A$3240 (3 )

Adventure Annapolis

2 2
B&B, Annapolis
Adventure Annapolis, a B&B, is located in Annapolis, 1.9 kilometres from Annapolis Harbour and 40 kilometres from Baltimore's Inner Harbour, Power Plant, and Convention Centre.
This accommodation offers 177 square metres of living space with two bedrooms, two bathrooms, and a guest capacity of 15, featuring air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, and a garden.
Near To Ccbc Essex Room 201 - Chesapeake Bay
9.5 2 reviews
Chesapeake Bay
29/08 – 05/09
A$156/nighttotal: A$1092 (7 )

Near To Ccbc Essex Room 201

1 2
B&B, Perry Hall
This Perry Hall guesthouse is conveniently located near the CCBC Essex campus, approximately 14-23 kilometres from various Baltimore attractions including universities and museums.
Offering one bedroom, one bathroom, and sleeping up to three guests, this self-catering property includes free Wi-Fi, air conditioning, parking, and towels/bed linen; a photo ID and credit card are required upon check-in.
3-story, Dog-friendly Home Near Beaches With Home Theatre, Grill & Gaming Tables - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
A$1409/nighttotal: A$8454 (6 )

3-story, Dog-friendly Home Near Beaches With Home Theatre, Grill & Gaming Tables

6 6
B&B, Highland Beach
This dog-friendly, three-storey guesthouse is located in Annapolis, a nine-minute walk from Bay Ridge Beach and 6.9 kilometres from Annapolis Harbour, with Baltimore-Washington International Airport situated 38.6 kilometres away.
This expansive B&B offers 700 square metres of living space, featuring six bedrooms accommodating up to 29 guests, a home theatre, gaming tables, a grill for outdoor cooking, and a garden, with air conditioning and Wi-Fi provided throughout.
The Blue House - Chesapeake Bay
9.0 3 reviews
Chesapeake Bay
05/07 – 08/07
A$191/nighttotal: A$573 (3 )

The Blue House

1 4
B&B, Dover
This Dover bed and breakfast, The Blue House, is located 4.3 kilometres from Dover International Speedway and within a 14-minute walk of Wesley College, providing easy access to Sewell C Biggs Museum of American Art (1.3 kilometres) and Schwartz Center for the Arts (11 minutes' walk).
This non-smoking guesthouse offers one bedroom, one bathroom, and can accommodate up to seven guests, with complimentary Wi-Fi, air conditioning, and on-site private parking available.
1896 Historic Bed & Breakfast Mansion With A General Store - Chesapeake Bay
9.8 8 reviews
Chesapeake Bay
30/07 – 05/08
A$1137/nighttotal: A$6822 (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.
Walton Haven - Chesapeake Bay
Chesapeake Bay
29/08 – 05/09
A$116/nighttotal: A$812 (7 )

Walton Haven

1 2
B&B, Newport News
Walton Haven B&B in Newport News offers convenient access to Busch Gardens (24km), Water Country USA (24km), and Newport News/Williamsburg International Airport (6km), alongside historical sites such as Colonial Williamsburg (32km) and Historic Jamestown (37km).
This guesthouse provides 24 square metres of accommodation, comprising one bedroom, one bathroom, sleeping up to two guests, and features complimentary Wi-Fi, private parking, and towels/bed linen.
Colonial Gardens B & B - Chesapeake Bay
9.8 6 reviews
Chesapeake Bay
30/07 – 05/08
A$1237/nighttotal: A$7422 (6 )

Colonial Gardens B & B

3 6
B&B, Williamsburg
Colonial Gardens B&B is situated in Williamsburg, just 4.3 kilometres from Colonial Williamsburg and 6.6 kilometres from Historic Jamestowne. The B&B enjoys an excellent location, cleanliness and user rating.
The guest house offers one bedroom and one bathroom. Guests can enjoy free Wi-Fi, on-site parking, a fitness room, garden views, a full English/Irish or American breakfast, mini-golf, cycling, fishing, canoeing and a garden.
Sweet And Beautiful Bedroom - Chesapeake Bay
8.1 28 reviews
Chesapeake Bay
29/08 – 05/09
A$145/nighttotal: A$1015 (7 )

Sweet And Beautiful Bedroom

1 2
B&B, Baltimore
This Baltimore guesthouse is situated near Johns Hopkins University, less than 1.1km from the Baltimore Museum of Art and within 5km of Clifton Park, the Walters Art Museum, and the Inner Harbour.
The 100 square metre property offers one bedroom, one bathroom, sleeping up to two guests, and features a fully equipped kitchen, in-unit laundry, free Wi-Fi, and private parking.
Inn At Huntingfield Creek - Chesapeake Bay
9.7 132 reviews
Chesapeake Bay
30/07 – 05/08
A$1140/nighttotal: A$6840 (6 )

Inn At Huntingfield Creek

2 6
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.
Cape Henry Full Suite Inn At Old Beach - Chesapeake Bay
10 5 reviews
Chesapeake Bay
05/07 – 08/07
A$825/nighttotal: A$2475 (3 )

Cape Henry Full Suite Inn At Old Beach

1 4
B&B, Virginia Beach
This Northeast Virginia Beach flat is situated a short walk from Pacific Avenue and the Virginia Beach Boardwalk, less than 0.8km from the Virginia Beach Convention Centre and Fishing Pier.
This 79 square metre, two-bedroom apartment sleeps six, boasting a fully equipped kitchen, two bathrooms (one en-suite), a private balcony, and access to a building hot tub; nearby attractions include the Virginia Beach Station, easily accessible by foot.
Historic Madison Ave - Chesapeake Bay
8.4 18 reviews
Chesapeake Bay
29/08 – 05/09
A$174/nighttotal: A$1218 (7 )

Historic Madison Ave

1 2
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.

Best Chesapeake Bay bed and breakfasts with breakfast included

Miller-dunham House B&b - Chesapeake Bay
10 106 reviews
Chesapeake Bay
29/08 – 05/09
A$368/nighttotal: A$2576 (7 )

Miller-dunham House B&b

1 2
B&B, Odessa
Miller-Dunham House B&B is located in Middletown, Delaware, just a short drive from historic attractions like the Old Dutch House and Dover International Speedway. The B&B has received excellent ratings for its location, cleanliness, and overall experience.
The charming inn offers a single bedroom with a private bathroom, comfortably accommodating two guests. Enjoy a variety of amenities including a garden, terrace, spa, and a kitchen, as well as free Wi-Fi, private parking, and a delicious breakfast with options to suit all dietary needs.
Hornsby House Inn - Chesapeake Bay
9.9 110 reviews
Chesapeake Bay
05/07 – 08/07
A$494/nighttotal: A$1482 (3 )

Hornsby House Inn

1 4
B&B, Yorktown
Hornsby House Inn is located in Yorktown, Virginia, just a short drive from Yorktown Beach, Busch Gardens & Water Country, and Colonial Williamsburg. The inn has consistently received excellent ratings for its location, cleanliness, and overall experience.
This charming guest house offers a peaceful garden setting with a private terrace and a bar. Guests can enjoy a delicious vegetarian or gluten-free breakfast, free Wi-Fi, and private parking, making it the perfect base for exploring the historic town and surrounding attractions.
George Brooks House B&b - Chesapeake Bay
8.5 140 reviews
Chesapeake Bay
05/07 – 08/07
A$944/nighttotal: A$2832 (3 )

George Brooks House B&b

2 4
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.
1840s Carrollton Inn - Chesapeake Bay
9.6 1232 reviews
Chesapeake Bay
30/07 – 05/08
A$905/nighttotal: A$5430 (6 )

1840s Carrollton Inn

2 6
B&B, Baltimore
The 1840s Carrollton Inn is located in Baltimore's Carrollton neighbourhood, within easy walking distance of attractions like the Power Plant and the National Aquarium. The inn has consistently received excellent ratings for cleanliness, location, and overall guest experience.
Each room in this charming guesthouse features air conditioning, a flat-screen TV with cable channels, and a private bathroom with a whirlpool spa bath. Guests can enjoy a range of amenities, including a garden, a terrace, a spa, a fitness centre, and a restaurant.

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

Coastal Comfort Retreat Near Annapolis, Ev Charger - Chesapeake Bay
9.9 211 reviews
Chesapeake Bay
02/07 – 05/07
A$270/nighttotal: A$810 (3 )

Coastal Comfort Retreat Near Annapolis, Ev Charger

1 2
B&B, Arnold
This guest suite is situated in Arnold, Maryland, just 6.4 kilometres from historic downtown Annapolis and the USNA, and 8 kilometres from Sandy Point State Park, making it a convenient base for exploring the area. The accommodation has received excellent ratings for cleanliness, location and user experience.
The self-contained suite can accommodate up to four guests and features a comfortable seating area, a king-size bed and a luxurious ensuite bathroom. Guests can enjoy access to a seasonal outdoor oasis with a swimming pool, hot tub, fire pit and a barbecue area, as well as a fitness centre, a private garden and a dedicated parking space.
Gramercy Mansion - Chesapeake Bay
9.7 205 reviews
Chesapeake Bay
05/07 – 08/07
A$849/nighttotal: A$2547 (3 )

Gramercy Mansion

2 4
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.
River Guest Suite W/ Pool, Beach, Private Boatslip - Chesapeake Bay
9.9 33 reviews
Chesapeake Bay
30/07 – 05/08
A$545/nighttotal: A$3270 (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.
Annapolis Garden Suite - Chesapeake Bay
9.9 128 reviews
Chesapeake Bay
05/07 – 08/07
A$490/nighttotal: A$1470 (3 )

Annapolis Garden Suite

2 4
B&B, Crownsville
This ground-floor self-contained apartment is located in a wooded residential area of Annapolis, Maryland, approximately 11 kilometres from restaurants and shops, 24 kilometres from the coast, 48 kilometres from Baltimore, and 56 kilometres from Washington, D.C.
The two-bedroom suite sleeps five, features a fully equipped kitchen with dishwasher, in-suite laundry, private pool, patio, and yard, high-speed Wi-Fi, and two private entrances.

Frequently asked questions about bed and breakfast in Chesapeake Bay

Destinations nearby

Best Chesapeake Bay bed and breakfasts with a garden

Cedars Of Williamsburg Bed & Breakfast - Chesapeake Bay
9.2 1347 reviews
Chesapeake Bay
29/08 – 05/09
A$306/nighttotal: A$2142 (7 )

Cedars Of Williamsburg Bed & Breakfast

1 2
B&B, Williamsburg
The Cedars of Williamsburg Bed & Breakfast is located just across the street from the College of William & Mary, a short walk from Colonial Williamsburg, offering a peaceful setting within easy reach of the city's historic attractions. The guesthouse has consistently received excellent ratings for its location, cleanliness, and overall experience.
The inn is housed in a historic Georgian brick building with unique furnishings and décor, creating a charming and authentic ambiance. Guests can enjoy a daily gourmet breakfast, relax in the on-site gardens, and explore the nearby dining options and attractions.
A Williamsburg White House Inn - Chesapeake Bay
9.5 279 reviews
Chesapeake Bay
29/08 – 05/09
A$426/nighttotal: A$2982 (7 )

A Williamsburg White House Inn

1 2
B&B, Williamsburg
A Williamsburg White House Inn is located in the historic district, just across the street from The College of William & Mary and within a 20-minute walk of Colonial Williamsburg. The inn has received excellent ratings for location, cleanliness and overall guest experience.
The inn is housed in a century-old estate and features rooms named after former US Presidents, each with a private bathroom. Guests can enjoy a complimentary full breakfast, afternoon snacks and wine, and free Wi-Fi throughout the property.
Carib Comfort B And B - Chesapeake Bay
Chesapeake Bay
02/07 – 05/07
A$346/nighttotal: A$1038 (3 )

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 Snuggery Inn & Suites Captain`s Quarters - Chesapeake Bay
10 2 reviews
Chesapeake Bay
29/08 – 05/09
A$725/nighttotal: A$5075 (7 )

The Snuggery Inn & Suites Captain`s Quarters

1 2
B&B, Easton
This St. Michaels flat, The Snuggery Inn & Suites, is situated in the town centre, offering immediate access to the St. Michaels Museum and Avalon Theatre, with the Chesapeake Bay Maritime Museum located 1.5 kilometres away.
This 56 square metre flat accommodates two guests, featuring one bedroom, one bathroom, air conditioning, internet, and a kitchen, with a complimentary stocked mini-refrigerator provided upon arrival.

Best Chesapeake Bay bed and breakfasts with air conditioning

Sweet Little Bedroom Next Fells Point - Chesapeake Bay
8.2 25 reviews
Chesapeake Bay
02/07 – 05/07
A$191/nighttotal: A$573 (3 )

Sweet Little Bedroom Next Fells Point

2 2
B&B, Baltimore
This Fell's Point guesthouse is situated approximately 1.6km from Pier Six Concert Pavilion and within walking distance of the historic Fell's Point neighbourhood in Baltimore, Maryland.
The 200 square metre property offers one bedroom, one bathroom, sleeping one guest, and includes air conditioning, towels, and bed linen; nearby attractions include the Harbor East Marina and the Sports Legends Museum at Camden Yards, both within 3.2km.
Wilson House Bed & Breakfast - Chesapeake Bay
9.6 151 reviews
Chesapeake Bay
02/07 – 05/07
A$201/nighttotal: A$603 (3 )

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.
Inn At Warner Hall - Chesapeake Bay
10 26 reviews
Chesapeake Bay
29/08 – 05/09
A$423/nighttotal: A$2961 (7 )

Inn At Warner Hall

1 2
B&B, Gloucester Point
The Inn at Warner Hall is a waterfront guesthouse situated in Gloucester Point, just 24 kilometres from historic Yorktown and 56 kilometres from Colonial Williamsburg. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The guesthouse is set on a 40-acre estate dating back to 1642, offering a unique glimpse into the region's history. Guests can enjoy a daily gourmet breakfast, relax in the gardens or on the porch, and take advantage of the boathouse for fishing or birdwatching.
The Inn At Tacaro Estate - Chesapeake Bay
9.0 29 reviews
Chesapeake Bay
05/07 – 08/07
A$1145/nighttotal: A$3435 (3 )

The Inn At Tacaro Estate

1 4
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.
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