Bed and breakfast vacation 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 favorite
Private room in Washington
4.99 out of 5 average rating, 376 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, 140 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 favorite
Private room in Chesapeake City
4.95 out of 5 average rating, 203 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 favorite
Private room in Baltimore
4.98 out of 5 average rating, 860 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 Norfolk
4.98 out of 5 average rating, 268 reviews

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

Showing my military family some much needed love! This special discounted rate is extended to active duty/retired service members, and their immediate family. As everyone knows, if you have a spouse or loved one in the military, the whole family is in the military! I have a private room with a queen sized bed and private bathroom in my home complete with flat screen TV, cable, Wifi and coffee in the morning for my military guys and gals! Need to get off base for a night or two? Come relax!

Top guest favorite
Private room in Dover
4.99 out of 5 average rating, 214 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
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, 244 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 favorite
A spacious living area features large windows allowing natural light to fill the room, highlighting the elegant stone fireplace. Modern furniture, including two black sofas and a wooden coffee table with flowers, creates a welcoming gathering space. A tall bookshelf displays decorative items and greenery.
Private room in Stafford
4.95 out of 5 average rating, 219 reviews

Falling Creek - Rm #2

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.

Guest favorite
Private room in Monrovia
4.85 out of 5 average rating, 142 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.

Guest favorite
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.
Condo in Lewes
4.95 out of 5 average rating, 57 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 favorite
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, 187 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 favorite
Guesthouse in Frederick
5 out of 5 average rating, 81 reviews

Quiet, Peaceful setting (suite 2)

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, 3-acre setting with free parking and amazing gardens. A short distance to downtown Frederick, the Frederick Station, Frederick Fairgrounds, and I-70.

Popular amenities for bed and breakfast rentals near Chesapeake Bay

Quick stats about bed and breakfast rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 90 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at G$8,367 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,440 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

    30 properties have a dedicated workspace

  • Wi-Fi availability

    90 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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