Bed and breakfast vacation rentals near Chesapeake Bay

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Top-rated bed and breakfast rentals near Chesapeake Bay

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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 Washington
4.99 out of 5 average rating, 350 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 favorite
Private room in Chesapeake City
4.92 out of 5 average rating, 289 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 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 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 favorite
Private room in Baltimore
4.98 out of 5 average rating, 810 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
Private room in Dover
4.99 out of 5 average rating, 209 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 favorite
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, 234 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.

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.
Apartment in Upper Marlboro
4.75 out of 5 average rating, 4 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 favorite
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
4.94 out of 5 average rating, 181 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.

Top guest favorite
Private room in Silver Spring
4.82 out of 5 average rating, 278 reviews

Peaceful Haven

My home is in a quiet, safe, suburban neighborhood. It is approximately a 20 minute drive to Washington DC and 15 minutes from downtown Silver Spring. The closest Metro station is an 8 minute drive. There is always parking available in my driveway. There are a variety of restaurants, groceries and shops close by. I am a warm, friendly person and will do everything I can to help you feel comfortable and welcome during your stay. The listing is in a private home.

Guest favorite
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 favorite
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.
Condo in Lewes
4.99 out of 5 average rating, 80 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.

Guest favorite
The exterior of a charming blue house is displayed, featuring a large porch and a bright turquoise door. A chimney rises from the roof under a clear blue sky, and two large windows provide ample light to the interior.
Place to stay in Catonsville
5 out of 5 average rating, 6 reviews

Cute efficiency 10 min from BWI and 5 min from 695

This unique place has a style all its own. A cat lovers dream Ever wanted to go to a cat café? We have a dozen kittens to snuggle! Brand new home! Immaculate. An efficiency suite upstairs in our cape code home. Walk up through kitchen. Charming bedroom stand up shower Cute sitting living room Roku Dishes provided hot plate, micro and dorm size fridge. To see full video vimeo dot com/1005209861

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.ﺇ294 per night before taxes and fees

  • Verified guest reviews

    Over 1,370 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!

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