Vacation rentals with a kayak in Kent County

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Top-rated kayak rentals in Kent County

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Guest favorite

The exterior of a rustic cabin is framed by lush green foliage. A covered porch with logs stacked nearby invites relaxation. The structure features a combination of wood siding and brick chimneys, showcasing the natural setting where it is nestled.

Farm stay in Chestertown

4.95 out of 5 average rating, 139 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 view of a paddleboarder gliding on calm water, with a spacious home featuring large windows in the background. Lush trees provide shade, and several outdoor seating areas are visible on the green lawn. Children can be seen playing near the water's edge.

Home in Chestertown

4.93 out of 5 average rating, 43 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

Guest favorite

A serene waterfront view is captured, showcasing calm waters reflecting the cloudy sky. A seating area with six chairs is positioned near a fire pit on a patio, with a swing nearby. The beach is lined with trees, creating a natural border.

Home in Middle River

4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

Guest favorite

A spacious dining area is shown with large windows exposing views of the tranquil water. A long wooden table is surrounded by eight chairs, while light wooden paneling complements the natural scenery. The sliding glass doors provide access to an outdoor deck.

Home in Rock Hall

4.96 out of 5 average rating, 51 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

This beautiful breathtaking waterfront home is the perfect place for your vacation. This spacious 3 story house sits along the back waters of the Chesapeake Bay, along Grey’s Inn Creek with it’s own private pier and beach area!! Kayaks and paddle boards available for guests to use! The water is 6’-9’ deep depending on the tide. You can bring your own boat or if you’re interested in renting one, Lankford Bay Marina is only 15 minutes by car or boat, must have a MD boaters safety card to rent

Top guest favorite

A modern, two-story home is surrounded by trees, featuring large windows that allow natural light to fill the interior. A wooden deck extends from the main level, providing access to an outdoor space. The house is elevated, supported by stilts, enhancing the scenic views.

Home in Rock Hall

5 out of 5 average rating, 35 reviews

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

Top guest favorite

A sandy beach area features several white Adirondack chairs arranged in a circle, alongside a fire pit and a small table. Surrounding greenery contributes to a natural landscape, while a wooden lifeguard chair stands nearby, overlooking the calm water.

Home in Stevensville

5 out of 5 average rating, 63 reviews

Love Point Idyll - 240' Private Beachfront

Spacious, comfortable vacation home located on Love Point, northern tip of Kent Island, in the heart of the upper Chesapeake. Beachfront property adjacent to former grounds of the historic Love Point Hotel grand resort, where well-to-do families once took steamboats from Baltimore piers to vacation in style (now Love Point State Park). On the coveted northeastern side of Kent Island, you have views of pleasure craft, fishing vessels, and an array of wildlife (including dolphins on occasion).

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 69 reviews

Waterfront w/ Hot Tub + Dock | Harbor View Haven

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

Superhost

A modern kitchen features light-colored cabinetry and a central island with seating for four. A clear glass pendant light hangs above, illuminating the space. A vase with blue and purple hydrangeas is positioned on the island, adding a touch of color to the space.

Home in Chestertown

5 out of 5 average rating, 3 reviews

Chesapeake Getaway | Marinas | Woodland Views

Escape to our peaceful retreat on Maryland's Eastern Shore, nestled in a quiet, wooded neighborhood near historic Chestertown. The Chesapeake Bay is known for its wildlife and serene landscapes. This cozy haven is perfect for unwinding and reconnecting with nature. After exploring Chestertown's charming streets, local shops, and delightful restaurants, or kayaking at nearby Worton Creek, relax in our comfortable home, where you can read, play games, or enjoy the peaceful surroundings.

Top guest favorite

Two green kayaks are securely stored on a wooden rack beside the river. Sunlight highlights their vibrant colors against the backdrop of gentle water and greenery. The serene environment invites water activities and relaxation by the riverside.

Home in Millington

5 out of 5 average rating, 19 reviews

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Top guest favorite

A well-maintained grassy area leads to the water's edge, framed by lush greenery. Two kayaks are positioned on the shore, ready for use. The calm river reflects the clear blue sky, creating a serene atmosphere.

Apartment in Chestertown

5 out of 5 average rating, 103 reviews

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

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, 221 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Guest favorite

A wooden dock extends over calm water, surrounded by lush greenery. Kayaks are visible alongside the dock, with trees providing a natural canopy above. The peaceful setting offers a serene space for recreation and enjoying nature.

Cabin in Worton

4.95 out of 5 average rating, 86 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.