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Holiday rentals with a kayak in Southern Maryland

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Top-rated Accommodation with a Kayak in Southern Maryland

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

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Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, 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, 148 reviews

Waterfront Chesapeake Bay Sunrises w/Private Pier!

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

4.96 out of 5 average rating, 26 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, 232 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, 165 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, 333 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 Shady Side

4.96 out of 5 average rating, 105 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

Guest favourite

Home in Deale

4.99 out of 5 average rating, 137 reviews

Chesapeake Waterfront HotTub-Kayaks-Crabbing

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups. Price is based on 4 add’l guests $20 per night pp.

Home in Scotland

4.91 out of 5 average rating, 126 reviews

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Guest favourite

Apartment in Cambridge

4.98 out of 5 average rating, 203 reviews

Private apt above garage w/ pier and water access

New 2 Bedroom apartment along the picturesque Choptank River. This quiet and spacious 2nd floor Private garage apartment features an open concept with 2 bedrooms, a full kitchen, living room, washer & dryer with optional garage area to store bikes or beach gear. Bike, walk or drive to local restaurants, parks and downtown attractions. Private beach and pier access!!! Close to all of the Ironman festivities and conveniently located to Rt 50. Kayaks on site.

Guest favourite

Home in Cambridge

4.98 out of 5 average rating, 121 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

Home in Cambridge

5 out of 5 average rating, 34 reviews

Serene getaway with great waterfront views!

Serene getaway with great waterfront views, private dock, and expansive deck. Located 10 minutes from Cambridge, MD, this home offers small groups and families a unique location with waterfront views throughout the house, updated spacious kitchen, kayaks, large back yard, grill for barbecue, and large dining and living rooms. Perfect for a quiet getaway to enjoy expansive views of the Choptank River at the mouth of Chesapeake Bay.

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Popular amenities for Southern Maryland kayak rentals

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

Guest favourite

Home in Woolford

4.93 out of 5 average rating, 139 reviews

Waterfront Getaway with Dock

Guest favourite

Home in Colonial Beach

4.94 out of 5 average rating, 17 reviews

Peaceful and Cozy Waterfront Home

Home in Heathsville

4.92 out of 5 average rating, 123 reviews

The Hideaway at Mill Creek

Guest favourite

Home in Lancaster

4.94 out of 5 average rating, 16 reviews

The River House

Home in Montross

4.91 out of 5 average rating, 160 reviews

Tranquil River Home

Guest favourite

Home in Newburg

4.9 out of 5 average rating, 112 reviews

The River House, a Wicomico Beach Retreat

Guest favourite

Home in Montross

4.99 out of 5 average rating, 144 reviews

Beach Please! River cottage w/private beach & dock

Home in Dunnsville

4.76 out of 5 average rating, 139 reviews

Cozy & Content River Retreat Beach Hot Tub & Games

Cottages with a kayak

Guest favourite

Cottage in Lancaster

4.93 out of 5 average rating, 30 reviews

Christmas Cottage on the River

Cottage in Reedville

4.88 out of 5 average rating, 189 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

Cottage in Warsaw

4.94 out of 5 average rating, 108 reviews

Modern 2 Bdrm Cottage in Historic River Community

Guest favourite

Cottage in Cambridge

4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

Guest favourite

Cottage in East New Market

4.95 out of 5 average rating, 58 reviews

Cottage on Cabin Creek

Guest favourite

Cottage in Hague

5 out of 5 average rating, 126 reviews

Potomac River cheerful cottage

Guest favourite

Cottage in Kinsale

5 out of 5 average rating, 31 reviews

River + Beach Front Cottage 4 BR ADA Northern Neck

Guest favourite

Cottage in Leonardtown

4.96 out of 5 average rating, 167 reviews

Beach Front and 'Perfectly Placed'

Cabin rentals with a kayak

Guest favourite

Cabin in Indian Head

4.97 out of 5 average rating, 29 reviews

*Private Waterfront Retreat w/3 Cabins Close to DC

Cabin in Reedville

4.7 out of 5 average rating, 20 reviews

"Elderberries" Chesapeake Bayfront Cottage

Cabin in Lancaster

4.88 out of 5 average rating, 51 reviews

Waterfront Log Home Retreat- Dock, Kayaks, Rest!

Cabin in Queenstown

4.89 out of 5 average rating, 19 reviews

Cozy Historic Cabin on the Water

Cabin in Saint Michaels

4.75 out of 5 average rating, 80 reviews

Cottage #4 Chesapeake Blue down the drive way.

Guest favourite

Cabin in Lusby

4.91 out of 5 average rating, 245 reviews

Peaceful Waterfront Retreat on The Bay

Guest favourite

Cabin in Lusby

4.93 out of 5 average rating, 181 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

Guest favourite

Cabin in Montross

4.96 out of 5 average rating, 23 reviews

Camp Heron : Waterfront Cabin on the Potomac

Destinations to explore