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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Guest favorite
Private room in Annapolis
4.84 out of 5 average rating, 475 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 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, 359 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
Private room in New Market
4.91 out of 5 average rating, 135 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.

Guest favorite
Private room in Chesapeake City
4.92 out of 5 average rating, 296 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 favorite
Private room in Silver Spring
4.9 out of 5 average rating, 265 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
Private room in Baltimore
4.98 out of 5 average rating, 838 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, 213 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
Private room in Washington
4.96 out of 5 average rating, 220 reviews

Charming bdrm in 110+yr home w/wood fireplace

Our home is in a great DC neighborhood minutes from Tenleytown/AU Red Line metro stop. You can easily walk to Starbucks, Whole Foods, 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. A wonderful breakfast for you to start your day is included..

Top guest favorite
Hotel room in New Castle
4.95 out of 5 average rating, 199 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.

Guest favorite
Private room in Monrovia
4.86 out of 5 average rating, 140 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, 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 favorite
Private room in Virginia Beach
4.92 out of 5 average rating, 203 reviews

Victorian Room (Queen & Full, private bath)

The Victorian Room at Parkside Retreat—a quiet, peaceful retreat just 3 miles from the bay and 5 miles from the oceanfront, without all the beach noise! Five minutes from I-264 in NE Virginia Beach. Huge back yard adjacent to park. We are very much like a classic bed and breakfast, just without the breakfast. We have three separate guest rooms available here at Parkside Retreat—see "Laura's Listings" in my profile to pick your favorite!

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.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,410 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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