
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.

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.

'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).

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.

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.

The White Oak Cabin
This 1850's one bedroom rustic cabin offers the option of 2 twin beds or 1 king (beds moved together with insert- upon request) and is ideal for history enthusiasts. A wood-burning fireplace adorns the downstairs, while the sleeping quarters are in the loft above. Decorated in period furnishings as well as an open air (no door) bathroom, visitors will get a more intimate look at our Country’s history. Pets are allowed and are charged a fee of $25 (first night) and $15 (per ea. add'l night).

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..

The Inn at Dirickson Creek- Room Two
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.

Falling Creek - Rm #4
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. 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.

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.
Popular amenities for bed and breakfast rentals near Chesapeake Bay
Family-Friendly Bed and Breakfasts

“Out to Sea” at the Terry House !

3 Private rooms in BnB, off- street parking

Cozy private room in Annapolis home

Military - Active/Retired/Family at Cape Defoe B&B

Lulabelle Room with Fireplace, Pool/Cabana

Smith Island Inn: Mary Ruth's Retreat

Stay right on Main Street Annapolis! Private room with double bed and bath.

Peaceful Farmette, Double Bedroom
Bed and breakfast rentals with breakfast

Mulberry in Lewes #2

Rustic & Elegant Private Bed & Bath

The Hummingbird Room - Sparkling Stars Inn

The Homestead B&B - Sea Glass Room

Aldrich House B&B Lewis Room

Gardenia Suite

Inspiration Room - Back INN Time

Gillis Grier Bed & Breakfast - The Pineapple Room
Bed and breakfast rentals with a patio

Chester Estates-Historic Mansion, Master Suite

Bright & Cozy Guest Suite with Private Kitchen

Room 35 at Rehoboth Guest House Bed and Breakfast

Naomi’s Bed & Breakfast~ Hot Breakfast Included!

Holland House B&B, Rm1 Mahogany

Quiet, Peaceful setting (suite 2)

Sunny Suite at Sam's on Semmes

USS Lawson
Other bed and breakfast holiday rentals

Paiton Room Lady Grace Bed and Breakfast

James - Colonial Capital Bed & Breakfast

Washington Suite - A Williamsburg White House

The Victorian Candle B&B Johnson Room

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

Bed & Breakfast at Rolling Hills Ranch

Bedroom with full bed in Quiet Shared Home

Wyatt House - peace and quiet in the country
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 $70 NZD per night before taxes and fees

Verified guest reviews
Over 1,440 verified reviews to help you choose

Pet-friendly accommodation
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

Wi-Fi availability
90 of Chesapeake Bay holiday 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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