
Bed and breakfast holiday rentals near Chesapeake Bay
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Top-rated bed and breakfast rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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.

'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).

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.

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.

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.

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.

Falling Creek - Rm #3
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.

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

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.

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.
Popular amenities for bed and breakfast rentals near Chesapeake Bay
Family-friendly bed & breakfast rentals

“Out to Sea” at the Terry House !

Cozy private room in Annapolis home

Rapunzel's Apartment on Washington St.

Lincoln Room w/ Private Entrance at Strawberry Inn

Eisenhower Suite at Olinger House

Beautiful Historic Home Near Gettysburg

Historic Civil War Farm House

Two peaceful rooms in leafy setting, EV charging
Bed and breakfast rentals with breakfast

3 Private rooms in BnB, off- street parking

Aldrich House B&B Lewis Room

The Homestead B&B - Orchard Room

The Victorian Candle B&B Johnson Room

Stay right on Main Street Annapolis! Private room with two twin beds and private bath.

EarthBound: Historic District 2nd Floor Suite

Speakeasy Quarters with Retro Arcade & Pool Access

Smith Island Inn: Mary Ruth's Retreat
Bed and breakfast rentals with a patio

Enjoy the good life, work & play

Chester Estates-Historic Mansion, Master Suite

Bright & Cozy Guest Suite with Private Kitchen

North Hanover * Close to Gettysburg

Holland House B&B, Rm1 Mahogany

The Commander’s Suites

The Rose Room/Spacious Victorian Inn

Large/private/high ceilings
Other bed and breakfast holiday rentals

Williamsburg Sampler - Lord Nelson Chamber

Rustic & Elegant Private Bed & Bath

Five Red Doors: Historic Hann House

Westmore Estate I: Oval BR in Gorgeous Modern B&B

Gardenia Suite

Orvis way Delta Unit

Second Floor bedroom With two queen beds.

The Anchorage Bed and Breakfast Skipjack
Quick stats about bed and breakfast rentals near Chesapeake Bay
Total rentals
80 properties
Nightly prices starting at
₹7,031 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
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