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.

%{current} / %{total}1 / 1
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, 352 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.

Guest favourite
Private room in Chesapeake City
4.92 out of 5 average rating, 293 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.

Guest favourite
Private room in Silver Spring
4.91 out of 5 average rating, 263 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
A charming historic building is seen from across the street, featuring a red exterior with decorative architectural details. Lush green trees provide shade, while a white picket fence borders the front garden filled with seasonal greenery and flowers. Nearby vehicles are parked along the street.
Flat in Richmond
4.93 out of 5 average rating, 356 reviews

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.

Top guest favourite
Private room in Baltimore
4.98 out of 5 average rating, 821 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
Private room in Dover
4.99 out of 5 average rating, 210 reviews

'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.

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, 235 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, 217 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.

Guest favourite
Private room in Monrovia
4.85 out of 5 average rating, 137 reviews

Quilt Room

The listing is for a room in a restored pre civil war farmhouse on Crickenwood Farm. Guest rooms are in the main farmhouse and share the common areas of the kitchen, library, living room and great room. This is a small working farm with cows and horses. There is plenty of parking. There are several friendly dogs on the property. The farm is about an hour from Baltimore, MD, Washington, DC, Harpers Ferry, WV and Gettysburg, PA. Frederick, MD is 20 mins.

Top guest favourite
A comfortable living area features a gray sofa with red accent pillows and two light upholstered chairs. A wooden coffee table is placed in the center, adorned with decorative items. Large windows allow natural light to fill the space, highlighting the original heart pine flooring.
Apartment in Lewes
4.99 out of 5 average rating, 81 reviews

Mulberry in Lewes

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.

Top guest favourite
The exterior of a multi-story apartment is displayed, featuring a wooden staircase leading to the upper level. A blooming pink tree adds a touch of color to the lush lawn, accompanied by black outdoor chairs set around a small table.
Flat in Cape May
4.98 out of 5 average rating, 242 reviews

Rapunzel's Apartment on Washington St.

Charming third floor apartment on beautiful Washington St. Walk to restaurants and shops, bike to the beach. Close to the Physick Estate and the Washington Inn, it's a great location. Apartment is bright, clean, and was completely re-done in 2020. Tastefully decorated with beautiful rugs, antiques and original art work. The carriage house on site is available to store bikes. Light breakfast is included.

Popular amenities for bed and breakfast rentals near Chesapeake Bay

Quick stats about bed and breakfast rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 80 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 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

    20 properties have a dedicated workspace

  • Wifi availability

    80 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