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Vacation rentals with a kayak in Kent Island

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Top-rated kayak rentals in Kent Island

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Top guest favorite
The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.
Farm stay in Chestertown
4.95 out of 5 average rating, 152 reviews

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville
4.95 out of 5 average rating, 285 reviews

River Front house / dock/hot tub

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Guest favorite
Two adirondack chairs in blue and teal are positioned on a wooden pier, facing the sunset over calm waters. A small white table sits between them, holding two coffee mugs. The vibrant orange and pink hues of the sky reflect on the water's surface.
Cottage in Edgewater
4.99 out of 5 average rating, 168 reviews

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Top guest favorite
The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.
Home in Shady Side
5 out of 5 average rating, 187 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Top guest favorite
A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.
Guest suite in Chestertown
4.99 out of 5 average rating, 239 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Guest favorite
The living space features a sofa with dark fabric, two plush recliners, and a small side table. A 42-inch flat-screen TV is centered against a decorative wooden wall unit. Natural light is filtered through two large windows covered with blinds.
Camper/RV in Sparrows Point
4.86 out of 5 average rating, 164 reviews

Cozy Camper, 2010 Brookstone RV - Waterfront

38 foot Fifth Wheel RV located at marina. Fully equipped kitchen, 1 bath and 1 bedroom with comfy King bed. Living space includes dinette with 4 chairs, sofa w/ full size air mattress and two recliners set up in front of a 42" flat screen TV. Heat and air provide the perfect accommodations no matter the weather. Enjoy sitting by the fire pit or explore the Bay on one of our two Kayaks. A stone's throw from Trade Point Atlantic, Key Bridge work site. Just 15-20 minutes to downtown Baltimore.

Superhost
The exterior of the farmhouse showcases a large, white structure with multiple windows and a spacious lawn surrounded by trees. The scene is complemented by a clear sky, creating a serene environment. Outdoor seating appears to be arranged on the patio, inviting relaxation.
Home in Chester
4.93 out of 5 average rating, 109 reviews

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in Saint Michaels
4.97 out of 5 average rating, 176 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Guest favorite
A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.
Apartment in Deale
4.91 out of 5 average rating, 620 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Top guest favorite
A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.
Guest suite in Pasadena
4.98 out of 5 average rating, 651 reviews

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Guest favorite
A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.
Guesthouse in Glen Burnie
4.93 out of 5 average rating, 363 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Top guest favorite
The interior space features a well-lit open layout with wooden beams overhead. A dining table sits to the left, while a living area with a comfortable sofa and coffee table is visible. Large windows provide ample natural light, enhancing the inviting atmosphere.
Cottage in Annapolis
4.98 out of 5 average rating, 130 reviews

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Popular amenities for Kent Island kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Guest favorite
An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.
Home in Riviera Beach
4.94 out of 5 average rating, 159 reviews

Waterfront Cheerful 5 home

Top guest favorite
A grassy yard extends to the water's edge, featuring several Adirondack chairs arranged for relaxation. Paths made of circular stones lead towards a private pier, where boats can be seen docked. Visible kayaks suggest opportunities for outdoor activities.
Home in Annapolis
4.98 out of 5 average rating, 62 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

Guest favorite
A waterfront home is depicted with a screened-in porch and a gabled roof. A wooden pier extends from the shore, leading to the water. Lush greenery surrounds the property, and stone embankments partially border the shoreline.
Home in Shady Side
4.95 out of 5 average rating, 115 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Superhost
A covered porch is shown with a hanging egg chair and a gray sectional sofa. Soft cushions are placed on the seating area. Beyond the railing, the tranquil waters of Chesapeake Bay can be seen, complemented by lush greenery and nearby homes.
Home in Annapolis
4.87 out of 5 average rating, 183 reviews

Charming Annapolis Water View Home

Top guest favorite
Adirondack chairs are arranged on the grassy waterfront, facing a serene view of the river at sunset. The sky displays a blend of warm orange and soft purple hues. A private pier extends into the water, with a boat docked nearby and calm reflections on the surface.
Home in Shady Side
4.98 out of 5 average rating, 65 reviews

Sunset Cottage

Superhost
A wooden dock extends into calm waters, leading to a two-story bayfront home adorned with large windows and a spacious deck. The surrounding landscape features lush greenery and a fenced yard, with boats visible on the water's edge under clear blue skies.
Home in Chester
5 out of 5 average rating, 7 reviews

Crab Alley | Waterfront Home + Hot Tub + Game Room

Superhost
A welcoming living room is presented, featuring two comfortable white armchairs flanking a central coffee table. Artwork with marine themes adorns the walls. A decorative blue and white rug covers the hardwood floor, while a fireplace adds warmth to the cozy space.
Home in Saint Michaels
4.83 out of 5 average rating, 12 reviews

Pet-Friendly Waterfront House

Top guest favorite
A scenic waterfront view is captured at sunset, showcasing colorful skies reflected on calm waters. Several boats are moored at the docks, with greenery lining the shore. A red kayak rests on the grassy bank, contributing to the serene atmosphere.
Home in Shady Side
5 out of 5 average rating, 10 reviews

A Happy Place

Cottage rentals with a kayak

Superhost
An inviting stone patio area features comfortable outdoor seating, framed by greenery. Light pours in through the open doors, leading to an interior space that includes minimalist decor and a spiral staircase. A hot tub is visible in the background, enhancing the tranquil setting.
Cottage in Annapolis
4.84 out of 5 average rating, 93 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale
4.95 out of 5 average rating, 169 reviews

Chesapeake Bay Cottage

Top guest favorite
A serene water view is captured as the sun sets, casting warm hues of orange and pink across the sky. The calm surface of the water reflects the colorful clouds, while a pier extends into the scene, inviting leisure and tranquility.
Cottage in Woolford
5 out of 5 average rating, 80 reviews

Waterfront Cottage & Guesthouse Near Cambridge

Guest favorite
A serene waterfront scene showcases a private dock extending into the water, framed by grassy areas. The horizon is painted with purple and orange hues from the setting sun, reflecting on the water's surface. Trees line the backdrop, adding to the tranquil atmosphere.
Cottage in Cambridge
4.98 out of 5 average rating, 51 reviews

Cozy Cottage on the Bay

Guest favorite
A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.
Cottage in Pasadena
4.97 out of 5 average rating, 186 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Top guest favorite
A serene view of a serene water landscape is showcased, featuring a double rainbow arching across the sky. Reflections of the rainbow are visible on the water's surface. A private pier extends into the water, surrounded by lush greenery.
Cottage in East New Market
4.96 out of 5 average rating, 72 reviews

Cottage on Cabin Creek

Top guest favorite
A scenic view is presented of a grassy area leading to a calm waterway. A sailboat glides across the water, while a dock with boats is visible. Lush trees frame the scene, creating a tranquil atmosphere.
Cottage in Saint Michaels
4.96 out of 5 average rating, 25 reviews

Very cosy and nicely appointed Waterfront Cottage

Top guest favorite
The exterior of a two-story historic home is showcased, featuring a light blue façade and white trim. A screened-in front porch is visible, along with a fresh American flag hanging from the porch. Lush greenery surrounds the property, enhancing its inviting appearance.
Cottage in Oxford
4.98 out of 5 average rating, 41 reviews

Historic Home in Heart of Oxford, MD

Cabin rentals with a kayak

Top guest favorite
An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.
Cabin in Saint Michaels
4.99 out of 5 average rating, 117 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

Superhost
The exterior of the historic cabin is showcased, featuring a dark blue facade with a white entrance door. Flowerpots flank the entrance, and landscaped gardens present vibrant floral hues. A glimpse of the dock along the river is visible in the background, framed by mature trees.
Cabin in Queenstown
4.93 out of 5 average rating, 27 reviews

Cozy Historic Cabin on the Water

Superhost
A serene coastal scene features a sandy beach lined with gentle waves. Overhanging branches with white flowers frame the view, while a distant pier is visible along the horizon. The sky is bright blue, accented with a few small clouds.
Cabin in Port Republic
4.76 out of 5 average rating, 17 reviews

Ocean Break

Superhost
A quaint cottage is presented with a welcoming porch and a light blue door. Lush greenery surrounds the structure, and a seating area with colorful chairs is visible on the lawn, providing a relaxed outdoor space for guests.
Cabin in Saint Michaels
4.76 out of 5 average rating, 82 reviews

Cottage #4 Chesapeake Blue down the drive way.

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