Bed and Breakfast and Inn in Chesapeake Bay

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

Best Chesapeake Bay bed and breakfasts with breakfast included

The Whitehaven Hotel - Chesapeake Bay
10 164 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.
Brampton 1860 - Chesapeake Bay
9.1 17 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.
Warner Hall - Chesapeake Bay
No reviews

Warner Hall

B&B, Gloucester Point
Warner Hall B&B, situated in Gloucester, offers pet-friendly lodging 9 kilometers from Gloucester city centre, providing a peaceful retreat outside the urban bustle.
This Gloucester Point guesthouse features one bathroom, accommodates two guests, and includes free Wi-Fi, on-site parking, and air conditioning.
Marvel's On The Creek - Chesapeake Bay
No reviews

Marvel's On The Creek

B&B, Secretary
Marvel's on the Creek, a guest house in East New Market, is located approximately 4 kilometres from the town centre, offering a peaceful retreat close to local amenities.
This pet-friendly lodging (USD 25 pet deposit applies) boasts a restaurant, Wi-Fi, parking, a terrace, and garden, accommodating up to two guests with one bathroom, and offers laundry services and tour assistance.

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

The Inn At Tacaro Estate - Chesapeake Bay
8.9 27 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.
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.
Bay Tree Manor - Chesapeake Bay
No reviews

Bay Tree Manor

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.
Gramercy Mansion - Chesapeake Bay
9.7 207 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.

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?

Popular destinations

Best Chesapeake Bay bed and breakfasts with a garden

Renovated, Dog-friendly Home With Private Pool, Hot Tub & Stunning Backyard - Chesapeake Bay
No reviews

Renovated, Dog-friendly Home With Private Pool, Hot Tub & Stunning Backyard

B&B, Lake Shore
This Pasadena guesthouse offers a lakeside location, situated 23 kilometres from Annapolis Harbour and 24 kilometres from Baltimore's Inner Harbour, the Power Plant, and Convention Centre, with Baltimore-Washington International Airport 13 kilometres away.
This dog-friendly B&B features four bedrooms and three bathrooms, accommodating up to 27 guests with amenities including a private swimming pool, hot tub, garden, and a fully equipped kitchen, plus a children's playground.
The Snuggery Inn & Suites Captain`s Quarters - Chesapeake Bay
10 2 reviews

The Snuggery Inn & Suites Captain`s Quarters

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.
Bay View Studio Apartment - Chesapeake Bay
9.9 160 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.
The Inn At Tacaro Estate - Chesapeake Bay
No reviews

The Inn At Tacaro Estate

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.

Best Chesapeake Bay bed and breakfasts with air conditioning

Rachael's Inner Harbor Boutique Inn - Chesapeake Bay
9.6 84 reviews

Rachael's Inner Harbor Boutique Inn

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.
The Towers Bed & Breakfast - Chesapeake Bay
9.9 199 reviews

The Towers Bed & Breakfast

B&B, Milford
The Towers Bed & Breakfast is located in Milford, Delaware, just 34 kilometres from Dover International Speedway and 40 kilometres from Rehoboth Beach Boardwalk. The establishment has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The accommodation offers a comfortable 26 square metre room with one bathroom. Guests can enjoy a range of amenities including free Wi-Fi, private parking, air conditioning, a relaxing garden, and a delicious full English/Irish or vegetarian breakfast.
A Williamsburg White House Inn - Chesapeake Bay
9.5 283 reviews

A Williamsburg White House Inn

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.
Luxury Farmette -Private & Secluded-1hr To Dc - Chesapeake Bay
10 116 reviews

Luxury Farmette -Private & Secluded-1hr To Dc

gîte, Aquasco
This luxurious farmhouse gîte, situated in Huntingtown, Maryland, is approximately 64km from Washington, D.C., offering a tranquil countryside escape near the city.
Sleeping eight guests, this self-catering property boasts four bedrooms, three and a half bathrooms, a fully equipped kitchen with walk-in pantry, a private pool, and extensive grounds including a children's playground and ample parking.
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