
Bed and breakfast holiday rentals near Chesapeake Bay
Find and book unique bed & breakfast rentals on Airbnb
Top-rated bed and breakfast rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Breakfast, Free Parking & Easy Walk to Mall, Wharf
DC Wharf, Anthem, National Mall & three Metro stations are within a 10-minute walk. The first floor is all yours. Very private. Your bathroom is stocked with amenities. Always fresh towels, clean sheets on a queen-size bed. Closets, wifi, laundry, courtyard view. Full access to the living room, dining room & kitchen on the second floor. We live on the third floor. Start the day with a fresh-ground coffee and a homemade breakfast. Happy to adjust to personal preferences and dietary restrictions.

Lincoln Room w/ Private Entrance at Strawberry Inn
Strawberry Inn is an 1837 home in the middle of the activity of Main Street in historic New Market, MD. Dining and coffee shops are in walking distance along with local jewelry, tea, and other shops. This ground-floor room has a private back porch entrance, king bed, WiFi, and private bath. Enjoy the garden and gazebo with a bottle of wine from a local vineyard. Breakfast snack bowl with fruit, breakfast bars, and Keurig are in the room. The Inn has been serving the Frederick region since 1973.

Cafe on the Bay - breakfast included!
We are in the heart of Chesapeake City on the C&D canal within walking distance of all the shops and restaurants. You will enjoy staying above the coffee shop so it’s best suited for early risers if you’re a light sleeer! We are a block away from the 3 wedding venues in town. The 2 bedrooms above the cafe are booked separately with a full bathroom in the hallway for guests to share. This is a great location for 2 couples or a family to book both rooms as it’s a shared bathroom for the 2 rooms.

Suburban Sanctuary
My home is in a quiet, safe, suburban neighborhood, approximately 20 minutes from Washington DC and 15 minutes from downtown Silver Spring. The closest Metro station is an 8 minute drive. It is a large two level ranch style home. Your bedroom and private bathroom will be on the main level where you enter the home. The kitchen, dining and living room reserved for guests is on the lower level which is above ground with a sliding glass door leading to the back patio. Driveway parking is available.

Historic Church Hill Gracious Apt-Balcony & Garden
Why stay in the ordinary when you can experience extraordinary? Fashionably furnished apt with private entry, courtyard, eat-in kitchen, washer/dryer, all amenities, fast Fios fiber-optic WiFi, free parking. In a desirable location - St. John's Church Historic District of Church Hill - charming urban village in the heart of a modern city. Guests tell us the apartment is quiet, relaxing and feels like home. A walkable neighborhood with restaurants. Guests can keep bikes inside a locked gate.

Guesthouse Bedroom 2/Private Parking - Mt. Vernon
Welcome to your 1874 mansion in the city, with off-street parking on premises! LGBTQ welcoming. The East Room is a KING bedroom with PRIVATE BATH. Located on the 2nd floor of an owner-occupied residence. You will not have to pass through my private living area, so you will experience the level of privacy, freedom to come and go, and professionalism expected in a B&B or guesthouse. There are 3 other rooms/suites available in my house. Unique space! Please review photos and the entire listing.

'Room J' for 1-2 guests in "Black Horse Inn"
Welcome to the 'Black Horse Inn'! Non-smoking home in quiet community. In- & outdoor cat. Close historic downtown, shops, dining, Air Base, NASCAR, casino, scenic Rt. 9 and the ocean. Quaint villages, wildlife parks, en route to the seashore. Room & shared bathroom in the loft; shared kitchen, dining area, outside seating. WiFi, Fire TV, Netflix. Breakfast! Room J Cozy room overlooking the back yard. Queen-size bed sleeps 2. Armoire and dresser for storage. Fold-out desk. Shared bathroom.

Mulberry in Lewes #2
Charming condominium in the midst of historic Lewes, Delaware converted from the original 1828 Bethel United Methodist Church. It is a spacious first floor unit with large rooms and high ceilings filled tastefully with vintage American furniture. The condominium is a short three block walk to downtown Lewes with its excellent restaurants and shops, and a 5-10 minute drive to the beaches of Delaware Bay, the Atlantic Ocean, and Cape Henlopen State Park.

The Inn at Dirickson Creek- Room Four
The Inn at Dirickson Creek is a newly renovated coastal casual bed and breakfast just 6 miles from Bethany Beach and Fenwick Island. Sitting on three and a half acres there is plenty of room for fun on days you decide to stick around. The inn offers six private bedrooms, private bath, four rooms offer private enclosed porches shared living room, and dining area. We also have a game room featuring a pool table, board games, and arcade games.

Beautiful Historic Home Near Gettysburg
Come enjoy a stay in comfortable, sunlit rooms close to historic Gettysburg, Hanover, Emmitsburg, Taneytown and Westminster. Full hot breakfast is served and included in your reservation. There are many restaurants, breweries and theaters nearby. We love to share our home with guests and to give tips on what to see while you’re here! When you get tired of sightseeing, the pool is a lovely place to relax.

Nance-Major Historic House
The Heart of Charles City on the Capital Trail. Halfway between Williamsburg and Richmond on scenic route 5. World famous Cul’s Courthouse Grille is directly next-door, with 12 local craft beer on tap, the best southern cuisine, and incredible live music every Friday, Saturday, and Sunday. Cul’s will make your stay one to remember.

Lovely Private Master Bedroom
A lovely, licensed and inspected, master bedroom, with kitchenette and deck, in the quiet Homewood/Southwoods neighborhood area of Annapolis. 2.5 miles from the downtown Market House. 1 mile from Navy Stadium. Easy access to rt 50 to Washington, DC or rt 97 to Baltimore.
Popular amenities for bed and breakfast rentals near Chesapeake Bay
Family-friendly bed & breakfast rentals

“Out to Sea” at the Terry House !

Cozy private room in Annapolis home

Military - Active/Retired/Family at Cape Defoe B&B

Falling Creek - Rm #2

Comfortable bdrm in 110+ yr old home w/large desk

Quilt Room

Five Red Doors: Historic Hann House

Hotel Room in Dupont Circle Washington DC
Bed and breakfast rentals with breakfast

3 Private rooms in BnB, off- street parking

Private 2BR Cottage with Breakfast - Cedars B&B

Rustic & Elegant Private Bed & Bath

The Homestead B&B - Sunflower Room

The Victorian Candle B&B Johnson Room

Gardenia Suite

Elegance Room - Back INN Time

Speakeasy Quarters with Retro Arcade & Pool Access
Bed and breakfast rentals with a patio

Bright & Cozy Guest Suite with Private Kitchen

Naomi’s Bed & Breakfast~ Hot Breakfast Included!

Holland House B&B, Rm1 Mahogany

Quiet, Peaceful setting (suite 2)

Sunny Suite at Sam's on Semmes

Wyatt House - peace and quiet in the country

B&B - Lawson

The Rose Room/Spacious Victorian Inn
Other bed and breakfast holiday rentals

Williamsburg Sampler - Lord Nelson Chamber

James - Colonial Capital Bed & Breakfast

10 Clarke B&B Poet's Loft

Chester Estates-Historic Mansion, Master Suite

Enchanted Cottage , farm, horses

Westmore Estate I: Oval BR in Gorgeous Modern B&B

Bed & Breakfast at Rolling Hills Ranch

Relaxing Country Elegance on Waterfront Property
Quick stats about bed and breakfast rentals near Chesapeake Bay

Total holiday rentals
Explore 90 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 1,440 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
90 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.8 Average rating
Chesapeake Bay stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Villa rentals Chesapeake Bay
- Flat rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Bed and breakfasts United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- The Mariners' Museum
- Nauticus
- Town Point Park
- Virginia Zoological Park
- Virginia Living History Museum
- Hampton University
- Cape Henry Light House
- Chrysler Hall





