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, 392 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.

Top guest favourite
Private room in Chesapeake City
4.95 out of 5 average rating, 205 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.

Top guest favourite
The exterior of the apartment building is highlighted by a charming Victorian-style structure with a peaked roof and decorative trim. A welcoming entrance is flanked by American flags, while lush greenery surrounds the property, creating a quaint and inviting atmosphere.
Flat in Richmond
4.93 out of 5 average rating, 366 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, 870 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
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, 251 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.

Guest favourite
Private room in Silver Spring
4.82 out of 5 average rating, 297 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 favourite
The exterior of the condominium is presented, showcasing a three-story white structure with large windows and a symmetrical facade. The entrance is framed by two sets of steps leading to double doors, surrounded by low-maintenance landscaping and trees providing subtle shade.
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.

Superhost
Private room in Stafford
4.93 out of 5 average rating, 134 reviews

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.

Top guest favourite
Private room in Littlestown
4.98 out of 5 average rating, 375 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.

Top guest favourite
Private room in Annapolis
4.98 out of 5 average rating, 244 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 $51 SGD 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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