Bed and Breakfast and Inn in Chesapeake Bay

280 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Chesapeake Bay B&B
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

280 Bed and Breakfasts and Inn in Chesapeake Bay

Best Chesapeake Bay bed and breakfasts with breakfast included

Solomons Victorian Inn - Chesapeake Bay
9.9 108 reviews
Chesapeake Bay
12/09 – 16/09
$390/nighttotal: $1560 (4 )

Solomons Victorian Inn

1 2
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.
Magnolia House Inn - Chesapeake Bay
9.8 22 reviews
Chesapeake Bay
23/08 – 28/08
$322/nighttotal: $1610 (5 )

Magnolia House Inn

1 2
B&B , Hampton
Magnolia House Inn is situated in Hampton, just a short drive from attractions like Busch Gardens, Colonial Williamsburg, and the Virginia Living Museum. The inn enjoys an excellent reputation, with guests consistently praising its cleanliness, location, and overall experience.
The inn offers comfortable rooms, each with a private bathroom, air conditioning, and a flat-screen TV. Guests can enjoy a delicious breakfast, relax in the garden, and take advantage of amenities like a bar, fitness centre, and free parking.
The Inn At Four Eleven York - Chesapeake Bay
10 150 reviews
Chesapeake Bay
23/08 – 28/08
$500/nighttotal: $2500 (5 )

The Inn At Four Eleven York

1 2
B&B , Norfolk
The Four Eleven York Suite is a charming bed and breakfast situated in the Ghent district of Norfolk, just a short walk from the Norfolk Botanical Garden and the Chrysler Museum of Art. This area is known for its lively atmosphere and proximity to cultural attractions. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The suite occupies the entire third floor of the inn, providing complete privacy with two bedrooms and two bathrooms. The suite features a range of luxurious amenities, including a California King bed, a fireplace, a stocked mini-bar, a rain shower head, heated flooring, and a private parlour with a Queen sleeper sofa.
Back Inn Time B&b - Chesapeake Bay
9.0 77 reviews
Chesapeake Bay
12/09 – 16/09
$285/nighttotal: $1140 (4 )

Back Inn Time B&b

1 2
B&B , Kilmarnock
Back INN Time B&B is located in Kilmarnock, a short distance from the town centre and within easy reach of the picturesque countryside. The B&B has excellent user, location and cleanliness ratings.
The accommodation is perfect for couples with one bedroom and a capacity of two guests. Guests can enjoy a garden with a terrace, modern bathrooms, free Wi-Fi, private parking and a delicious breakfast with a variety of options.

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 Haven Harbour - Chesapeake Bay
8.6 4 reviews
Chesapeake Bay
07/10 – 11/10
$479/nighttotal: $1916 (4 )

Inn At Haven Harbour

1 2
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.
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.
George Brooks House B&b - Chesapeake Bay
8.5 140 reviews
Chesapeake Bay
23/08 – 28/08
$431/nighttotal: $2155 (5 )

George Brooks House B&b

1 2
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.
Superb Location! 4 Posh Units, Pet-friendly - Chesapeake Bay
Chesapeake Bay
20/06 – 27/06
$1365/nighttotal: $9555 (7 )

Superb Location! 4 Posh Units, Pet-friendly

4 13
B&B , Baltimore
This charming bed and breakfast is located in Baltimore's Inner Harbour district, just a short walk from the National Aquarium, the Maryland Science Centre and Oriole Park at Camden Yards. The area is bustling with activity, offering a vibrant mix of shops, restaurants and attractions.
The property has four bedrooms and four bathrooms, accommodating up to 16 guests. Guests can enjoy a range of amenities including a swimming pool, fitness centre, and a restaurant and bar.

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

The Snuggery Inn & Suites Sea Grass Room - Chesapeake Bay
10 1 review
Chesapeake Bay
12/09 – 16/09
$415/nighttotal: $1660 (4 )

The Snuggery Inn & Suites Sea Grass Room

1 2
B&B , Easton
This Sea Grass Room flat in St. Michaels is situated within meters of shops, eateries, nightspots, and museums, with local landmarks such as the St. Michaels Museum and Avalon Theatre in close proximity.
This 19 square meter studio flat accommodates two guests, offering a private en-suite bathroom, complimentary stocked mini-refrigerator, air conditioning, and on-site parking, with exclusive use of the West Parlor for added communal space.
Hornsby House Inn - Chesapeake Bay
9.9 110 reviews
Chesapeake Bay
12/09 – 16/09
$393/nighttotal: $1572 (4 )

Hornsby House Inn

1 2
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.
Dog-friendly House With Yard, Deck, Firepit, Washer- Dryer & Ac - Near Golf - Chesapeake Bay
Chesapeake Bay
01/10 – 05/10
$924/nighttotal: $3696 (4 )

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

2 3
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.
Va Beach Zen Retreat House - Chesapeake Bay
8.1 9 reviews
Chesapeake Bay
20/06 – 27/06
$844/nighttotal: $5908 (7 )

Va Beach Zen Retreat House

2 13
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.

Best Chesapeake Bay bed and breakfasts with air conditioning

Inn At Warner Hall - Chesapeake Bay
10 26 reviews
Chesapeake Bay
20/06 – 27/06
$416/nighttotal: $2912 (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.
Adventure Annapolis - Chesapeake Bay
Chesapeake Bay
20/07 – 27/07
$853/nighttotal: $5971 (7 )

Adventure Annapolis

2 4
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.
Ma Margarets House Bed And Breakfast - Chesapeake Bay
9.7 32 reviews
Chesapeake Bay
23/08 – 28/08
$203/nighttotal: $1015 (5 )

Ma Margarets House Bed And Breakfast

1 2
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.
4 Rooms Off I-95 W/ On-site Restaurant & Breakfast - Chesapeake Bay
Chesapeake Bay
20/06 – 27/06
$407/nighttotal: $2849 (7 )

4 Rooms Off I-95 W/ On-site Restaurant & Breakfast

4 13
B&B , Edgewood
This Edgewood guesthouse is conveniently located near Junction 95 of the I-95 highway, offering easy access to Harford Glen Park and the Anita C. Leight Estuary Center, both within a short driving distance.
The four-bedroom, four-bathroom property sleeps up to sixteen guests, providing four separate rooms ideal for groups; on-site amenities include a restaurant, fitness centre, and laundry facilities, plus complimentary breakfast and Wi-Fi.
©2026 cozycozy.com