Bed and breakfast in Chesapeake Bay

537 available b&b offers

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

Popular Bed and Breakfasts by the Sea in Chesapeake Bay

Find seashore B&Bs in Chesapeake Bay for a charming stay steps from the ocean.

Gorgeous & Bright Retreat With Patio, Firepit, Wd, & Stunning Rooftop Views - Chesapeake Bay
No reviews

Gorgeous & Bright Retreat With Patio, Firepit, Wd, & Stunning Rooftop Views

B&B, Annapolis
This Annapolis bed and breakfast is situated 1.8 kilometres from Annapolis Harbour, providing straightforward access to Baltimore's Inner Harbour and Power Plant attractions, located 32 kilometres away, with Baltimore-Washington International Airport 29 kilometres distant.
This spacious 78 square metre guesthouse offers one bedroom, three bathrooms, and accommodates up to eleven guests, featuring air conditioning, a fully equipped kitchen with a fridge and microwave, an in-unit washer and dryer, a private patio with a firepit, and rooftop views.

Popular Bed and Breakfasts in the CBD in Chesapeake Bay

Stay right where local island life, dining, and beaches come together at central bed and breakfasts in Chesapeake Bay.

Airstream Farm Stay Cape Charles - Chesapeake Bay
9.9 294 reviews

Airstream Farm Stay Cape Charles

gîte, Cape Charles
This Airstream studio is situated on a historic Eastern Shore farm, just 10 kilometres from Cape Charles and 45 kilometres from Virginia Beach/Norfolk, offering a peaceful retreat surrounded by nature. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The studio is perfect for a couple or small family, with a modern design and a spacious deck for relaxing or working remotely. Guests can enjoy the farm's amenities, including a garden, trails, and the chance to interact with farm animals, as well as the proximity to Kiptopeke State Park and fishing grounds for outdoor activities.
Back Inn Time B&b - Chesapeake Bay
9.2 81 reviews

Back Inn Time B&b

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.
Cricket Hill House  Waterfront Suite, 2 East - Chesapeake Bay
10 4 reviews

Cricket Hill House Waterfront Suite, 2 East

B&B, Gwynn
Cricket Hill House is a boutique waterfront inn situated on Gwynn's Island, offering expansive views of Milford Haven and the Chesapeake Bay, just 500 metres from Hole in the Wall Waterfront Grill and Bar and within 1.6 kilometres of The Hatchery Oyster Eatery.
This guest house provides private suites with kitchenettes and air conditioning, along with direct pier access and proximity to Gwynn's Island Museum and local amenities, accommodating up to two guests.
Inn At Warner Hall - Chesapeake Bay
10 34 reviews

Inn At Warner Hall

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.

Frequently asked questions about bed and breakfast in Chesapeake Bay

Popular destinations

Best Chesapeake Bay bed and breakfasts with breakfast included

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.
Hornsby House Inn - Chesapeake Bay
9.9 109 reviews

Hornsby House Inn

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.
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.
Naomi Bed And Breakfast - Chesapeake Bay
No reviews

Naomi Bed And Breakfast

B&B, Carney
Naomi B&B, located in Parkville, offers convenient access to Towson University, situated 9.2 kilometres away, and is within 14.5 kilometres of Clifton Park and the Baltimore Museum of Art.
This family-friendly guesthouse provides air-conditioned accommodation with free Wi-Fi, free private parking, a garden, and a terrace, featuring units with flat-screen televisions and private bathrooms, some of which include balconies.

Best Chesapeake Bay bed and breakfasts with parking

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking - Chesapeake Bay
No reviews

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

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.
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.
Newcastle 106 Inn At Old Beach - Chesapeake Bay
10 1 review

Newcastle 106 Inn At Old Beach

B&B, Virginia Beach
B&B with an excellent rating of 100% based on 1 reviews. You will be in Virginia Beach.
Facilities and services include a terrace, a washing machine and a fridge. Enjoy free parking with this accommodation in Virginia Beach!
Rachael's Inner Harbor Boutique Inn - Chesapeake Bay
9.6 88 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.

Popular Bed and Breakfasts with a Swimming Pool in Chesapeake Bay

Take a refreshing freshwater swim surrounded by tropical flowers at island B&Bs featuring a pool in Chesapeake Bay.

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
Escape To Our Beachfront Oasis | Private Beach - Chesapeake Bay
9.2 635 reviews

Escape To Our Beachfront Oasis | Private Beach

B&B, Virginia Beach
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
Inn At Huntingfield Creek - Chesapeake Bay
9.8 104 reviews

Inn At Huntingfield Creek

B&B, Rock Hall

Best Chesapeake Bay bed and breakfasts with air conditioning

Blue Heron Inn - A Bed And Breakfast Llc - Chesapeake Bay
9.8 7 reviews

Blue Heron Inn - A Bed And Breakfast Llc

B&B, Solomons
Colonial Gardens B & B - Chesapeake Bay
9.8 7 reviews

Colonial Gardens B & B

B&B, Williamsburg
Sweet And Beautiful Bedroom - Chesapeake Bay
8.3 30 reviews

Sweet And Beautiful Bedroom

B&B, Baltimore
Exclusive Waterfront Getaway - Chesapeake Bay
9.9 35 reviews

Exclusive Waterfront Getaway

B&B, Broomes Island

See Guest-Favourite Premium Bed and Breakfasts in Chesapeake Bay

Experience premium coastal hospitality with elegant rooms and private beach access at luxury island B&Bs in Chesapeake Bay.

1896 Historic Mansion With A General Store - Chesapeake Bay
9.8 8 reviews

1896 Historic Mansion With A General Store

apartment, Newport News

Best Chesapeake Bay bed and breakfasts with a garden

The Towers Bed & Breakfast - Chesapeake Bay
9.9 199 reviews

The Towers Bed & Breakfast

B&B, Milford
Private 3 Room Queen Suite W/kitchenette - Chesapeake Bay
9.9 112 reviews

Private 3 Room Queen Suite W/kitchenette

apartment, Port Deposit
Riverfront Chalet Kayak/canoe, Pier, Breakfast! - Chesapeake Bay
10 387 reviews

Riverfront Chalet Kayak/canoe, Pier, Breakfast!

B&B, Solomons
Guest Quarters At The Inn - 205 - Chesapeake Bay
9.8 251 reviews

Guest Quarters At The Inn - 205

apartment, North Beach
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