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

Swanendele Inn - Chesapeake Bay
9.6 85 reviews

Swanendele Inn

B&B, Piney Point
Swanendele Inn, a beachfront guesthouse in Ridge, Maryland, boasts stunning views and is situated 6.4km from Clayton Marina and 14km from St. Mary's College of Maryland.
This one-bedroom, one-bathroom inn offers guests a spa, concierge service, free Wi-Fi, private parking, and a delicious American breakfast, alongside convenient amenities including a fireplace, walk-in showers, and a paid airport shuttle to Ronald Reagan Washington National Airport (126km).
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.
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.
Parsonage Inn - Chesapeake Bay
9.2 137 reviews

Parsonage Inn

B&B, Easton
This charming guesthouse in St. Michaels is a short walk from the Chesapeake Bay Maritime Museum and St. Michaels Winery, offering a peaceful escape in a picturesque setting. It has consistently received excellent guest reviews.
The property features a garden and a library for relaxing, and offers a range of amenities including a swimming pool, a terrace, and free parking. Guests can enjoy a complimentary full breakfast, concierge services, and free Wi-Fi in public areas.

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

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.
Splendid Home With Private Pool, Fire Pit, Several Decks & Balconies - Chesapeake Bay
No reviews

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

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.
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.
Dockside Inn - Chesapeake Bay
9.4 53 reviews

Dockside Inn

B&B, Deltaville
This guesthouse offers seaside proximity and is situated within 2 kilometres of the Deltaville Maritime Museum, Holly Point Nature Park, and Deltaville Marina, with Chesapeake Bay 2.2 kilometres away.
Guests can enjoy complimentary bicycles for local exploration, free WiFi in public areas, and an on-the-go breakfast, with housekeeping available upon request.

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

Elk Forge Bed And Breakfast - Chesapeake Bay
8.5 264 reviews

Elk Forge Bed And Breakfast

B&B, Elkton
This Elkton bed and breakfast is located just six miles from the University of Delaware and a short drive from Newark, Delaware, offering a peaceful retreat away from the city. It has consistently received very good ratings for its location, cleanliness, and overall experience.
The property features spacious rooms, each with a unique design, a sitting area, and a fireplace. Guests can enjoy a range of amenities including a spa with a hot tub, a gourmet breakfast, barbecue facilities, and a business centre.
Historic 1825 Chesapeake Farm Stay - Chesapeake Bay
No reviews

Historic 1825 Chesapeake Farm Stay

B&B, Long Beach
This family-friendly bed and breakfast is located in Long Beach, within 10 kilometres of Perigeaux Winery and Matoaka Beach, and close to Chesapeake Bay.
Guests can enjoy complimentary continental breakfast, free Wi-Fi in common areas, and complimentary non-valet parking, with gas barbecues and a picnic area available for outdoor dining.
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.
The Snuggery Inn & Suites Captain`s Quarters - Chesapeake Bay
10 3 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.

Best Chesapeake Bay bed and breakfasts with air conditioning

The Princess Anne 200 Inn At Old Beach - Chesapeake Bay
No reviews

The Princess Anne 200 Inn At Old Beach

B&B, Virginia Beach
B&B. You will be located in Virginia Beach.
Services and facilities include a washing machine, free parking and air conditioning. Take advantage of the terrace in this accommodation!
Dog-friendly House With Yard, Deck, Firepit, Washer- Dryer & Ac - Near Golf - Chesapeake Bay
No reviews

Dog-friendly House With Yard, Deck, Firepit, Washer- Dryer & Ac - Near Golf

B&B, Annapolis
This dog-friendly guesthouse in Annapolis is located 2.7 kilometres from Annapolis Harbour and 29 kilometres from Baltimore's Inner Harbour.
The accommodation offers two bedrooms, three bathrooms, and a capacity for nineteen guests, featuring a fully equipped kitchen, air conditioning, a private garden, and a fire pit, with the convenience of an in-unit washer and dryer.
Sweet And Beautiful Bedroom - Chesapeake Bay
8.4 31 reviews

Sweet And Beautiful Bedroom

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.
Private | Near Baybridge | Wedding Venue Proximity - Chesapeake Bay
10 1 review

Private | Near Baybridge | Wedding Venue Proximity

B&B, Stevensville
This guest house in Stevensville is situated near BayBridge, offering convenient access to the Eastern Shore and lying 26 kilometres from Baltimore/Washington International Airport, with Annapolis Harbour a further 26 kilometres away.
This one-bedroom, one-bathroom B&B spans 74 square metres, accommodates up to seven guests, and features air conditioning, free WiFi, a kitchen with a fridge and microwave oven, and complimentary private parking.
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