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.

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Top guest favourite
Private room in Washington
4.99 out of 5 average rating, 388 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 favourite
Private room in New Market
4.91 out of 5 average rating, 141 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 favourite
Private room in Chesapeake City
4.95 out of 5 average rating, 204 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.

Guest favourite
Private room in Silver Spring
4.89 out of 5 average rating, 273 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, 365 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, 867 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, 216 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 favourite
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.
Apartment in Lewes
4.95 out of 5 average rating, 58 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.

Guest favourite
A cozy bedroom is defined by a spacious bed with crisp white bedding. Light wood accents and a ceiling with natural wood paneling create a soothing environment. Two bedside lamps provide soft illumination, and large glass doors open to a private enclosed porch.
Private room in Frankford
4.94 out of 5 average rating, 190 reviews

The Inn at Dirickson Creek- Room Four

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.

Top guest favourite
Private room in Littlestown
4.98 out of 5 average rating, 374 reviews

Beautiful Historic Home Near Gettysburg

Come enjoy a stay in comfortable, sunlit rooms close to historic Gettysburg, Hanover, Emmitsburg, Taneytown and Westminster. Full hot breakfast is served and included in your reservation. There are many restaurants, breweries and theaters nearby. We love to share our home with guests and to give tips on what to see while you’re here! When you get tired of sightseeing, the pool is a lovely place to relax.

A charming two-story house is presented with a white exterior and green accents. A covered porch with white railings extends across the front. Surrounding landscape includes low shrubs and trees, adding a natural touch to the inviting entrance.
Home in Charles City
4.9 out of 5 average rating, 10 reviews

Nance-Major Historic House

The Heart of Charles City on the Capital Trail. Halfway between Williamsburg and Richmond on scenic route 5. World famous Cul’s Courthouse Grille is directly next-door, with 12 local craft beer on tap, the best southern cuisine, and incredible live music every Friday, Saturday, and Sunday. Cul’s will make your stay one to remember.

Top guest favourite
Private room in Annapolis
4.98 out of 5 average rating, 242 reviews

Lovely Private Master Bedroom

A lovely, licensed and inspected, master bedroom, with kitchenette and deck, in the quiet Homewood/Southwoods neighborhood area of Annapolis. 2.5 miles from the downtown Market House. 1 mile from Navy Stadium. Easy access to rt 50 to Washington, DC or rt 97 to Baltimore.

Popular amenities for bed and breakfast rentals near Chesapeake Bay

Quick stats about bed and breakfast rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 90 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 1,440 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

    30 properties have a dedicated workspace

  • Wifi availability

    90 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!

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