Top 10 Coolest Waterfront Airbnbs in Maryland - stays and getaways (2024)

Lusby, MD – 3 Bedrooms – Avg Nightly Rate $221

“Listed on the National Register of Historic Places and cared for by the Calvert Marine Museum (CMM), the Cove Point Lighthouse historic site has been lovingly restored and re-purposed so that it can be enjoyed by all. The active lighthouse and keeper’s home sit on a seven-acre point of land in one of the narrowest points of the Chesapeake Bay. Proceeds from this beautiful rental site will support the CMM and a lighthouse endowment set up for its continued care.”

View Listing on Airbnb You can also check them out on Instagram

Ocean City, MD – 2 Bedrooms – Avg Nightly Rate $307

“The Tiny House on Fisherman Lane may be tiny, but it’s full of functional space. Enjoy relaxing and entertaining in the open concept living, kitchen, and dining space while view wonderful water views from the end of the canal.”

View Listing – – Or book this property directly through Nolen Vacation Rentals. You can also check this property out on Facebook andInstagram

Lusby, MD – 4 Bedrooms – Avg Nightly Rate $464

“Rousby Hall is located on the Patuxent River, outside of Solomon’s Island with a view of the river’s opening to the Chesapeake Bay. The 10-acre property is adjacent to a very private, 6 acres of conservation area. The year-round property has its own private beach, pier, pool (April-Oct) with amazing river views. Co-owner, Chef Robert Wiedmaier, (Marcel’s, Brasserie Beck+) is available to cook dinners, steam crabs, fresh catch & more.”

View Listing – You can also check this property out onInstagram

Rock Hall, MD – 2 Bedrooms – Avg Nightly Rate $200

“Serene space nestled in the woods; with water views. You have your own private cottage on our 10 acre property to watch the sunsets and enjoy the nature all around. The cottage is warm cozy with lovely amenities. There is a pool table to test your skills, relax in the steam shower or jacuzzi tub. Sit and unwind enjoying the water views of the Swan Creek. You will surely love our peaceful, cozy little cottage and all it has to offer!”

View Listing – You can also check this property out on Facebook and Instagram

Arnold, MD – 3 Bedrooms – Avg Nightly Rate $525

“This newly updated mid-century modern home offers a peaceful retreat from the brisk pace of everyday life. The home sits approximately 45′ above Chase Creek on a spectacular piece of land surrounded by acres of open space, but just minutes from downtown Annapolis and major routes. Whether you relax in the living room while taking in the views, explore the river, or enjoy the nearby hike and bike trails, this home will suit your vacation needs.”

View Listing – You can also check this property out on Facebook and Instagram

Saint Michaels, MD – 1 Bedroom – Avg Nightly Rate $302

“La Casita is an architecturally unique newly constructed guesthouse on a secluded 40-acre farm on Harris Creek, just off the Chesapeake Bay. 5 min by car to historic St Michaels. Featuring a bedroom loft, with an open design concept and 360 views.La Casita is proof positive one can stay in luxury, be at one w/ nature, and still be close enough to delight in the fine dining, shops & outdoor wonder that is St Michaels.”

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Chestertown, MD – 2 Bedrooms – Avg Nightly Rate $320

“Situated on the Chesapeake Bay with wonderful views from The Carriage House and its private patio, this is not to be missed for a private or family friendly stay. Use your leisure to kayak, canoe or paddle board to explore the Chesapeake. Bike the quiet country roads or walk the tree shaded lanes. This modern space boasts a two-level living space with a living room, dining room and gourmet kitchen. All the upstairs windows show the magnificent views of the Bay. This is the perfect place for your stay.”

View Listing on Airbnb – I highly recommend booking this property directly through Great Oak Manor for the best possible rate, the carriage house is among many beautiful accommodation options offered at their B&B property. You can also check them out on Facebook and Instagram.

Ocean Pines, MD – 4 Bedrooms – Avg Nightly Rate $151

“Your vacation experience will be truly memorable at this uniquely round home with bright and fresh decor and an electric fireplace. Enjoy the comforts of your surroundings or launch your kayaks and SUPs from the dock for a little water adventure. The outside seating offers fresh air, tranquil views, and plenty of space for relaxing meals. With all the amenities of home, your vacation will be carefree as the stress of daily life melts away!”

View Listing – This property is additionally owned and managed by Vacasa Maryland, visit their official site to compare rates and view other properties.

Annapolis, MD – 2 Bedrooms – Avg Nightly Rate $359

“This brand-new condo houseboat is nestled in Back Creek. The views of the Chesapeake Bay are amazing! This is the best place to see the sunrise from the roof top deck while sipping a cup of coffee. The houseboat is kept on a boat lift which is suspended above the water. Even though the houseboat is stationary on a lift, the boat does have some movement and will sway with wind.”

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Edgewater, MD – 1 Bedroom – Avg Nightly Rate $400

“The brand-new Gemini Studio Houseboat is the most comfortable floating studio apartment you have ever seen! A brand-new houseboat that is laid out like a high-end NYC studio apartment in a gated resort marina. You will be surrounded by amazing views and gorgeous decor. Lounge on the back deck watching the sunset, relax in the sun on the roof top deck, and get rocked to sleep by the waves at night.”

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