Bed and breakfast vacation rentals near Chesapeake Bay

Find and book unique bed and 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.

1 of 1 pages1 / 1
Guest favorite
A cozy cottage is surrounded by lush greenery and features a well-kept lawn. Two bright green chairs are positioned on a stone pathway leading to the entrance, inviting relaxation. Warm lights glow from the windows, creating a welcoming ambiance.
Private room in Annapolis
4.84 out of 5 average rating, 478 reviews

Cozy private room in Annapolis home

Come enjoy a furnished cozy cottage in sought after Historic Annapolis, Maryland. ..the sailing capital of the east coast. Accommodations are simple with open decking and private entrance to bedroom area. A trundle day bed makes into two twins or double bed with little room to spare.A single bath will be shared along with kitchen privileges. The house is situated in a quiet neighborhood with no need for a car. Although parking is in front of the house if you do have a car. A walking path and biking trail run throughout the area. There is easy public transportation(trolley) to downtown and harbor area. You also may choose to walk to the nearby Historic area downtown and the Naval Academy Stadium and yard. Within walking distance there are restaurants and shopping with something in mind for everyone. Enjoy Annapolis at your leisure being adventurous or relaxed. You are welcome to my home with a lovely deck outside your room and Odin(young,nosey, English Cream Golden Retriever) to enjoy. We always look forward to meeting new guests. Media: includes internet access/basic cable television available upon request. Pets: Negotiable Meals: Coffee/Tea, light breakfast fare

Top guest favorite
A view showcases the town's buildings alongside a calm waterfront, with a large bridge extending overhead. Green trees dot the landscape, and the clear blue sky complements the serene setting, reflecting the charm of Chesapeake City.
Private room in Chesapeake City
4.95 out of 5 average rating, 213 reviews

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.

Top guest favorite
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 Southwest Washington
5.0 out of 5 average rating, 406 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 favorite
The historic 1837 home features a white exterior with green shutters and a prominent gabled roof. Red, white, and blue bunting adorns the front porch, enhancing its classic charm. A bright red sports car is parked in front, adding a pop of color to the façade.
Private room in New Market
4.92 out of 5 average rating, 143 reviews

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.

Top guest favorite
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.
Apartment in Church Hill
4.93 out of 5 average rating, 376 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.

Guest favorite
A spacious bedroom is furnished with a large bed, a wooden desk, and a comfortable armchair. Natural light filters through two large windows, draped with gold curtains. A nightstand and an upholstered bench add functional touches to the inviting space.
Private room in Silver Spring
4.9 out of 5 average rating, 282 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 favorite
The historic mansion is displayed with a beautifully aged red brick facade, accented by intricate architectural details. Tall windows provide ample natural light, while the multi-gabled roof adds character. Two cars are parked on the street in front, complementing the tree-lined setting.
Private room in Baltimore
4.98 out of 5 average rating, 885 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 favorite
A cozy room features wood-paneled walls and a spacious bed covered with a quilt. A small entertainment unit holds a television, with shelves displaying books and decorative items nearby. Natural light filters in through a window adorned with dark curtains.
Private room in Dover
4.99 out of 5 average rating, 222 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.

Guest favorite
The exterior of the spacious brick home features a symmetrical design with multiple large windows, accented by black shutters. A welcoming front entrance is highlighted by a broad staircase leading up to a covered porch, framed by neatly trimmed shrubs and a well-maintained lawn.
Private room in Stafford
4.95 out of 5 average rating, 224 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 favorite
A spacious living area features a mix of vintage and modern furnishings. A comfortable gray sofa is complemented by two light-colored armchairs. Decorative pillows add a subtle touch of color. A patterned area rug covers the hardwood floor, while natural light streams through large windows.
Condo in Lewes
4.95 out of 5 average rating, 59 reviews

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.

Top guest favorite
A large tree stands prominently on a lush green lawn, casting soft shadows on the grass. In the background, a charming yellow house is partially visible, surrounded by manicured landscaping and the serenity of the expansive grounds.
Guesthouse in Frederick
4.98 out of 5 average rating, 83 reviews

Quiet, peaceful setting (suite 1)

A beautiful experience! Built in 1896, fully restored in 2022, our guest house provides a private, 1 bdr/1 ba suite with kitchenette in an upscale neighborhood. An exceptionally private, park-like, peaceful, guest-available 3-acre setting with free parking and amazing gardens. Located a short distance to downtown Frederick, the Frederick Station, Frederick Fairgrounds, and I-70. This property is very near Frederick, but a true Garden of Eden.

Guest favorite
A spacious bedroom features a large four-poster bed dressed in a light-colored floral quilt. Two bedside lamps provide soft illumination. A wooden dresser and a mirror add warmth, while a comfortable armchair and a small side table offer additional seating. Natural light enters through large windows.
Private room in Frankford
4.93 out of 5 average rating, 126 reviews

The Inn at Dirickson Creek- Room One

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.

Popular amenities for bed and breakfast rentals near Chesapeake Bay

Quick stats about bed and breakfast rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 80 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 1,290 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Chesapeake Bay vacation 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!

Destinations to explore