Bed and Breakfast and Inn in Chesapeake Bay

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Chesapeake Bay B&B
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280 Bed and Breakfasts and Inn in Chesapeake Bay

Best Chesapeake Bay bed and breakfasts with breakfast included

The Yellow Rose Of Talbot Bed And Breakfast - Chesapeake Bay
9.7 183 reviews
Chesapeake Bay
23/08 – 28/08
$239/nighttotal: $1195 (5 )

The Yellow Rose Of Talbot Bed And Breakfast

1 2
B&B , Easton
The Yellow Rose of Talbot Bed and Breakfast is located in Easton, Maryland, just 2.9 kilometres from the Academy of the Arts and a short drive from the Federalsburg Marina. The property enjoys excellent ratings for location, cleanliness and overall experience.
The charming guesthouse offers one bedroom and one bathroom, accommodating up to two guests. Guests can enjoy a variety of amenities, including free Wi-Fi, private parking, a garden, a spa and an outdoor fireplace.
Miller-dunham House B&b - Chesapeake Bay
10 105 reviews
Chesapeake Bay
29/08 – 05/09
$361/nighttotal: $2527 (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.
Wades Point Inn On The Bay - Chesapeake Bay
9.6 143 reviews
Chesapeake Bay
29/08 – 05/09
$445/nighttotal: $3115 (7 )

Wades Point Inn On The Bay

1 2
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.
Rachael's Inner Harbor Boutique Inn - Chesapeake Bay
9.2 28 reviews
Chesapeake Bay
01/10 – 05/10
$670/nighttotal: $2680 (4 )

Rachael's Inner Harbor Boutique Inn

1 3
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

Gramercy Mansion - Chesapeake Bay
9.7 205 reviews
Chesapeake Bay
23/08 – 28/08
$280/nighttotal: $1400 (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
$354/nighttotal: $1770 (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
01/10 – 05/10
$1042/nighttotal: $4168 (4 )

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

4 3
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.
Bay Tree Manor - Chesapeake Bay
Chesapeake Bay
30/07 – 05/08
$1253/nighttotal: $7518 (6 )

Bay Tree Manor

3 6
B&B , Poquoson
Bay Tree Manor, a guesthouse in Seaford, is situated 29 kilometres from Busch Gardens and Water Country and 39 kilometres from Colonial Williamsburg, offering convenient access for day trips.
This family-friendly establishment provides complimentary WiFi, air conditioning, a swimming pool, a Jacuzzi, and a spa, with breakfast options including Full English/Irish or American, and fishing opportunities nearby.

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, you should definitely check out the Chesapeake Bay Bridge, a stunning landmark connecting the Eastern Shore to the mainland. You could also visit the Annapolis Maritime Museum, which is a great way to learn about the history of the bay. If you're interested in nature, a visit to the Eastern Neck National Wildlife Refuge is worth it.
  • 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?

    St. Michaels is a charming town with plenty of bed and breakfasts, offering a relaxed atmosphere and easy access to the bay. Annapolis is another great option, with a historic downtown and a vibrant waterfront, though it tends to be more expensive than St. Michaels.
  • 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?

    There are many great restaurants in Chesapeake Bay, but for solo travellers, I'd recommend trying out the Chesapeake Inn in Grasonville. It's a classic seafood restaurant with a relaxed atmosphere and plenty of options for solo diners. If you're staying in St. Michaels, the St. Michaels Crab House is a popular choice with a wide selection of fresh seafood.
  • 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 hosts a variety of cultural events throughout the year, including concerts, festivals, and workshops. Annapolis is also a great place for cultural activities, with the Annapolis Symphony Orchestra, the Maryland State House, and the US Naval Academy. If you're visiting in the summer, be sure to check out the Bay Days festival, which is held in various locations around the bay.
  • 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?

    The Bay Country Trail is a great option for hiking and exploring the natural beauty of the Chesapeake Bay region. The trail stretches for over 400 kilometres and offers stunning views of the water and surrounding forests. There are also several shorter trails in state parks and wildlife refuges.
  • 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?

    Most bed and breakfasts in Chesapeake Bay offer a range of amenities, including a hearty breakfast, free Wi-Fi, and parking. Some bed and breakfasts also have swimming pools, hot tubs, or fire pits, depending on the property. It's always best to check the individual bed and breakfast's website for specific amenities.
  • What are the best bed and breakfasts with parking in Chesapeake Bay?

Destinations nearby

Best Chesapeake Bay bed and breakfasts with a garden

Ma Margarets House Bed And Breakfast - Chesapeake Bay
9.7 32 reviews
Chesapeake Bay
01/10 – 05/10
$341/nighttotal: $1364 (4 )

Ma Margarets House Bed And Breakfast

1 3
B&B , Heathsville
Ma Margaret's House Bed and Breakfast is situated in Reedsville, a peaceful village just 88 kilometres from Richmond International Airport. It has received excellent ratings for its location, cleanliness, and overall experience.
The guest house offers a comfortable and relaxing stay with a choice of rooms featuring air conditioning, satellite TVs, and private bathrooms. Guests can enjoy a full country breakfast, relax on the terrace or in the garden, and benefit from free Wi-Fi and on-site parking.
Carib Comfort B And B - Chesapeake Bay
Chesapeake Bay
20/07 – 27/07
$764/nighttotal: $5348 (7 )

Carib Comfort B And B

2 4
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.
2-story Downtown Home With Enclosed Yard, Deck, Firepit, Gas Grill & Fireplace - Chesapeake Bay
Chesapeake Bay
20/07 – 27/07
$792/nighttotal: $5544 (7 )

2-story Downtown Home With Enclosed Yard, Deck, Firepit, Gas Grill & Fireplace

3 4
B&B , Annapolis
This 2-storey downtown Annapolis guesthouse is located an 11-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This property offers 251 square metres of living space with 3 bedrooms, 4 bathrooms, and a capacity for 15 guests, featuring a private enclosed garden with a deck, firepit, gas grill, and a children's playground.
Colonial Gardens B & B - Chesapeake Bay
9.8 6 reviews
Chesapeake Bay
29/08 – 05/09
$382/nighttotal: $2674 (7 )

Colonial Gardens B & B

1 2
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.

Best Chesapeake Bay bed and breakfasts with air conditioning

Va Beach Zen Retreat House - Chesapeake Bay
8.1 9 reviews
Chesapeake Bay
30/07 – 05/08
$334/nighttotal: $2004 (6 )

Va Beach Zen Retreat House

1 6
B&B , Virginia Beach
The VA Beach Zen retreat house is located in Virginia Beach, just a short drive from Topgolf Virginia Beach and Mount Trashmore Park, making it a convenient base for exploring the area. The property has received very good user ratings and excellent ratings for location and cleanliness.
The retreat offers a comfortable and relaxing stay with a 149 square metre floor area. Guests can enjoy a shared lounge area, a garden, and a terrace, as well as a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and private parking.
1896 Historic Bed & Breakfast Mansion With A General Store - Chesapeake Bay
9.8 8 reviews
Chesapeake Bay
30/07 – 05/08
$1117/nighttotal: $6702 (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.
On Ensor - Chesapeake Bay
9.0 240 reviews
Chesapeake Bay
01/10 – 05/10
$326/nighttotal: $1304 (4 )

On Ensor

2 3
B&B , Baltimore
On Ensor is a charming bed and breakfast located in a residential area of Baltimore, just 1.6 kilometers from Penn Station and within 3.2 kilometers of The Walters Art Museum, Clifton Park, and Historic Ships in Baltimore. This property has received very good user ratings, with excellent marks for cleanliness and a good location rating.
The bed and breakfast has one bedroom and one bathroom, accommodating up to two guests. Each room features free Wi-Fi, air conditioning, a flat-screen TV, a fridge, and a coffee machine, ensuring a comfortable and convenient stay.
Sigiriya Lodge - Chesapeake Bay
Chesapeake Bay
23/08 – 28/08
$75/nighttotal: $375 (5 )

Sigiriya Lodge

1 2
B&B , Cockeysville
Sigiriya Lodge, a guest house in Carney, offers a convenient base for exploring Cockeysville, situated 29 kilometres from the town centre.
This Cockeysville B&B provides en-suite accommodation for two guests, featuring Wi-Fi, parking, a restaurant, bar, room service, a garden, and a barbecue area, plus laundry and tour assistance services.
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