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

Historic Civil War Farm House
The David Stewart Farm is located in historic Gettysburg, PA. The farmhouse & barn were used as a civil war field hospital immediately after the Battle of Gettysburg. Located 4 miles from the center of town, it's an easy drive to the battlefields, local attractions and local restaurants. Baltimore is about 1 hour away and Washington, DC is 1 1/2 hours. You will be staying in a large sunny room with a queen-size bed and have your own private bathroom (shower, no tub). There is a second smaller bedroom (with 2 twin beds) that can be used if you have 3 or 4 people in your group. The kitchen and family room will be shared with me and my pets - currently 1 large dogs and 5 cats. They do have the run of the house so if you do not like pets or are allergic to or afraid of animals, this is probably not the best place for you. (There are many other great Airbnb places to stay in Gettysburg that are pet free.) There is a large deck and big backyard (100 acres) for you to hang out if the weather permits. There are a couple of miles of trails around the farm that you can hike or mountain bike. If you enjoy fishing, bring your poles along! There is a large pond with lots of bass, sunnies and catfish! I will be your only "living" host, but there are many others who reside with me. They have lived at the farm for many many years, some for hundreds of years. Yes, the house is haunted, but they are all friendly! I have been here for 36 years and have lots of interesting stories that I'd be happy to share with you if you are interested.

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.

Comfortable bdrm in 110+ yr old home w/large desk
Our home is in a great DC neighborhood min. from Tenleytown/AU Red Line metro stop. You can easily walk to Starbucks, Whole Foods Market, CVS, and many other shops and eateries along with American University's main campus within 10 min. AU Law School is a 5 min walk and downtown DC is a 15 min metro ride. You’ll love our home w/its fabulous kitchen, comfortable bedrooms, warm atmosphere, and amazing front porch and deck. Included is a wonderful breakfast for you to start your day.

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.

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 and Breakfasts

“Out to Sea” at the Terry House !

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

Falling Creek - Rm #2

Quilt Room

Five Red Doors: Historic Hann House

Beautiful Historic Home Near Gettysburg

Two peaceful rooms in leafy setting, EV charging

Dormer House - Shannon Room
Bed and breakfast rentals with breakfast

3 Private rooms in BnB, off- street parking

Rustic & Elegant Private Bed & Bath

The Hummingbird Room - Sparkling Stars Inn

Aldrich House B&B Lewis Room

The Homestead B&B - Cottage

Hotel Room in Dupont Circle Washington DC

Second Floor bedroom With two queen beds.

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

Bright & Cozy Guest Suite with Private Kitchen

North Hanover * Close to Gettysburg

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

Eisenhower Suite at Olinger House

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

Williamsburg Sampler - Lord Nelson Chamber

James - Colonial Capital Bed & Breakfast

Chester Estates-Historic Mansion, Master Suite

RiverTreehouse Suite

Inspiration Room - Back INN Time

Gillis Grier Bed & Breakfast - The Pineapple Room

George Brooks House #3 King Jacuzzi

The Anchorage Bed & Breakfast
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 $56 AUD per night before taxes and fees

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

Pet-friendly accommodation
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

Wi-Fi availability
90 of Chesapeake Bay holiday rentals include Wi-Fi 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!
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