Bed and breakfast holiday rentals near Chesapeake Bay

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Top-rated bed and breakfast rentals near Chesapeake Bay

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Top guest favourite
Private room in Gettysburg
4.93 out of 5 average rating, 670 reviews

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.

Top guest favourite
A sunlit sunroom features a green sofa and a red armchair, both positioned to enjoy the views of the surrounding greenery. Large windows provide ample natural light and a sense of openness, while a potted plant adds a touch of nature indoors.
Private room in Washington
4.99 out of 5 average rating, 342 reviews

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.

Top guest favourite
Two baby goats are observed on a bed of straw beside their mother. One goat stands with its back facing the camera, while the other is positioned closer to the mother. The goats display soft fur in shades of white and brown.
Farm stay in Frederick
5 out of 5 average rating, 81 reviews

Historic Bed & Breakfast - Central (Suite 2)

New baby goats in 2025! A beautiful experience! Our 1896 original Frederick farmhouse and carriage house, restored in 2022, provides a private, 1-bedroom, 1-bathroom guest house suite with kitchenette in upscale neighborhood. A private, park-like, peaceful, 4-acre setting with free parking, amazing gardens, and owners providing in-room breakfast from onsite gardens, vineyard, and orchard (seasonally). A short distance to downtown Frederick, the Frederick Station, Frederick Fairgrounds, and I-70.

Guest favourite
Private room in Chesapeake City
4.92 out of 5 average rating, 286 reviews

Cafe on the Bay 2- 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.

Top guest favourite
Private room in Dover
4.96 out of 5 average rating, 147 reviews

'Room D' for 2-6 guests in "The Black Horse Inn"

Welcome to the 'Black Horse Inn'! Non-smoking home in quiet community. In- & outdoor cat. Close to historic downtown, shops, dining, Air Base, NASCAR, casino, scenic Rt 9 and the ocean. Quaint villages, wildlife parks, en route to DE seashore. Private room, shared loft bathroom, dining area, inside & outside seating. WiFi, Fire TV, Netflix. Breakfast! Possibly kitchen use. Room D Full-size bed, full-size futon sofabed, 2 twin beds available, sleeps 4 or even 6 (bed: 2, futon: 2, twin beds: 2).

Top guest favourite
Private room in Silver Spring
4.91 out of 5 average rating, 256 reviews

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.

Top guest favourite
Private room in Baltimore
4.98 out of 5 average rating, 791 reviews

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.

Top guest favourite
A spacious front porch is furnished with a variety of comfortable seating options, including a large sofa and several wicker chairs adorned with green cushions. A glass-topped table sits in the center, complemented by standing lamps that enhance the serene environment, surrounded by greenery.
Private room in Washington
4.99 out of 5 average rating, 230 reviews

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.

Two wooden chairs sit on a stone patio, facing a small table. The surrounding area is lush with greenery from the forest, creating a serene setting. Moss covers the stones, enhancing the rustic charm of the outdoor space.
Guest suite in Quarryville
4.99 out of 5 average rating, 157 reviews

In a Forest - Ensuite with Separate Entrance

We have a three story A-frame in a small forest in southern Lancaster County. You get the entire downstairs area which has a separate entrance, private bathroom, sitting area, bedroom, and limited kitchen (refrigerator, freezer, microwave, and coffee/tea kettle). The surrounding area is rural, peaceful and quiet. Lancaster City is 15 miles to the north, Philadelphia 60 miles to the east, and Baltimore 60 miles to the south. Please read the Disclaimer below BEFORE you book.

Top guest favourite
A spacious living area features large windows allowing natural light to fill the room, highlighting the elegant stone fireplace. Modern furniture, including two black sofas and a wooden coffee table with flowers, creates a welcoming gathering space. A tall bookshelf displays decorative items and greenery.
Private room in Stafford
4.95 out of 5 average rating, 210 reviews

Falling Creek - Rm #2

Welcome to Falling Creek, conveniently located less than 3 miles from I95. Less than an hour drive from D.C. and only 10 - 15 min from Quantico and Downtown Fredericksburg where you can walk around to shop, eat or have a drink. Unlike some other places, we don't require you to perform any chores or cleaning before checking out. Your comfort and satisfaction are our top priorities. Feel free to take your time, savor your last moments, and leave any tidying up to us.

A bright living area features a modern sectional sofa adorned with decorative pillows in navy and white. A minimalist floor lamp stands beside the couch, complementing the artwork on the wall that displays a map. Natural light enters through the window, enhancing the space.
Flat in Upper Marlboro
5 out of 5 average rating, 3 reviews

3 BEDR, Inground Pool, Close To D.C

Escape to Tranquility on 9+ scenic acres just minutes from DC, National Harbor, and the Upper Marlboro Equestrian Center. Our beautifully appointed four bedrooms and two baths guest house offers, comfort, privacy, and an unforgettable setting This estate is perfect for those who enjoy peaceful morning, or relaxing in the evening surrounded by nature. The full-property rental includes: • 3 luxurious bedrooms • Full bathroom • Fully equipped kitchens • Living room

Top guest favourite
The entrance to The Terry House is framed by a sturdy black door adorned with intricate carvings. A welcoming sign hangs beside the door, and the steps are flanked by neatly trimmed shrubs in black planters, adding an inviting touch to the historic brick façade.
Hotel room in New Castle
4.95 out of 5 average rating, 169 reviews

“Out to Sea” at the Terry House !

The Terry House, a Federal Townhouse circa 1860, is located in historic New Castle, Delaware. This room is on the 2nd floor, featuring a historical nautical theme in one room and historical classic cars in the other room. This suite features, a queen and a full beds as well as private baths and a mini fridge in each room. There is a common area space called the parlor room on the first floor to work, hangout, or play games. ** Not serving breakfast at the moment.

Popular amenities for bed and breakfast rentals near Chesapeake Bay

Quick stats about bed and breakfast rentals near Chesapeake Bay

  • Total rentals

    80 properties

  • Nightly prices starting at

    $104 SGD before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore