Holiday rentals with a kayak in Southern Maryland

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Southern Maryland

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite

Home in Mechanicsville

5 out of 5 average rating, 67 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Superhost

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is near, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 151 reviews

Waterfront Chesapeake Bay Sunrises w/Private Dock!

Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.

Guest favourite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Cottage in Kinsale

4.93 out of 5 average rating, 236 reviews

Great little cottage with a "Rivah" view

Welcome to our little slice of paradise on the Yecomoco river. This off the beaten path location has easy access into the Potomac for Rockfish or a little further into the Bay itself. Our dock can be used to swim, fish, crab or just relax and enjoy. A nice little marina is conveniently located nearby to put your boat into the river. Come and enjoy "Rivah" life at its finest. Unwind relax and enjoy. But if you do need to do a little work while you are here, we do have hi speed internet.

Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 168 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Guest favourite

Guest suite in Lusby

4.98 out of 5 average rating, 335 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Guest favourite

Home in Lottsburg

4.93 out of 5 average rating, 67 reviews

Nirmal Cottage Serene River Retreat with bay view

Slow down! Enjoy your morning coffee watching the sunrise over the Chesapeake bay, catch a playful dolphin pod. Cottage is perfect for couples or family. Surrounded by open water & woods home to bald eagles, ospreys this is a perfect getaway from crazy schedules and timelines. Enjoy the laid back pace, go antiquing visit quaint towns. The cottage has all the modern amenities. End the day with a glass of wine and catch the sunset. Cottage is a hidden gem to witness both sunsets & Sunrises

Guest favourite

Home in White Stone

4.81 out of 5 average rating, 53 reviews

Beach House with Private Beach, Kayak, and Canoe

"A beautiful beach house with 580 feet of water frontage. Scenic views from every room. Tucked in a private peninsula and featuring a private beach, the 3-bedroom, 2-bath vacation rental boasts 2300 square feet of space designed for rest and relaxation. When you're not admiring the view from the floor-to-ceiling windows or large furnished deck, spend a relaxing day out in one of the provided kayaks and canoe of your coastal paradise, just 1.5 hours from Richmond and 2.5 hours from D.C.!"

Guest favourite

Home in Cambridge

4.98 out of 5 average rating, 123 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Guest favourite

Cottage in Onancock

4.96 out of 5 average rating, 110 reviews

Little Cottage on the Creek

Experience Onancock....."a little slice of nowhere else". Whether you are looking for a romantic getaway for two, or just some rest and relaxation off the beaten path, Little Cottage on the Creek is the perfect place for your stay. Beautifully furnished and freshly renovated, this cozy waterfront cottage has all the comforts of home. Enjoy magnificent views of Onancock Creek along with the serenity for which the Eastern Shore is famous.

Superhost

Home in Cambridge

4.9 out of 5 average rating, 103 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!