Holiday rentals with a kayak in Talbot County

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Top-rated rentals with kayak in Talbot County

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

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Top guest favourite

An elevated view of a green two-story house is surrounded by tall trees, with water visible in the background. The layout includes a wraparound porch and landscaped shrubbery, leading to a winding drive that approaches the front entrance.

Guest house in Saint Michaels

5 out of 5 average rating, 41 reviews

Secluded water, private sitting room, full bath!

Come by land or by Broad Creek! 125' dock. 1000' waterfront. 2 miles from St. Michael's. A perfect getaway for discerning guests. Ask to moor a small vessel (sorry, no trailers). Natural, secluded, private entrance. Ideal kayaking, biking and walking. Eagles, ospreys, herons, ducks, turkey, fox, rays, crabs, oysters... and when very lucky, dolphins! Hosts available for convenience, but not in your space. *PET: If breed preapproved, $90/visit up to 4 days for ONE small dog. $15/day thereafter.

LocationOutdoor spacesCleanliness

Top guest favourite

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, 195 reviews

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

Outdoor spacesValueBathroom

Guest favourite

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

4.93 out of 5 average rating, 124 reviews

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Outdoor spacesValueKitchen

Guest favourite

Lush green grass leads to the waterfront, where the calm water reflects the surroundings. Two white Adirondack chairs sit invitingly under the shade of tall trees, providing a serene spot for relaxation. A wooden dock extends into the water, enhancing the picturesque setting.

Home in Neavitt

4.94 out of 5 average rating, 104 reviews

Waterfront, Dog friendly, St Michaels home

Lovingly restored waterfront historic home just minutes from St. Michaels. Located in a quiet waterman's village, Seth's Landing provides tranquility and beautiful surroundings. Up for a little adventure? Bring your watercraft of choice - house has dock with two deepwater boatslips. Or bring your bikes - great area for biking! Or rent any of these from local business and have delivered to house. Great for couples and small families. Due to proximity to water, not good for young children.

Outdoor spacesValueParks

Top guest favourite

A wooden pier extends over gentle waters, surrounded by rocks. The scene is illuminated by a soft pink and orange sky at sunset, reflecting on the water's surface. Additional pilings can be seen in the distance, enhancing the tranquil setting.

Home in Cambridge

5 out of 5 average rating, 61 reviews

• Peaceful Point • A relaxing waterfront retreat

Welcome to Peaceful Point! Come enjoy the beauty of the water and the serenity it brings at Peaceful Point. This brand new remodel is fresh on the market with 3 bedrooms, 2 bathrooms, and custom great room with vast views of the Choptank River from every seat. Enjoy the screened in porch over looking the cove, a vast yard, deck and pier to crab and fish, as well as kayak and paddle board. Privately located yet only 20 minutes from restaurants + shopping. Come relax with the family at PP!

LocationOutdoor spacesGrill

Guest favourite

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, 197 reviews

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay 100ft away. Water views from most rooms plus treehouse vibes. 4 bedrooms + 4 full bath. Custom luxury upgrades, new appliances. Pull out daybed +2 folding queen mattresses, rustic leather sectional sofas can sleep 4 more (14+total), outdoor grills, covered balconies, hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

ValueLocationBathroom

Top guest favourite

Home in Stevensville

5 out of 5 average rating, 21 reviews

Waterfront | Swim Spa + Sauna + Beach + Game Room

Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

LocationOutdoor spacesFamily

Top guest favourite

A modern guest barn is situated amidst a serene farm setting, with a sleek metal roof and large windows. The exterior features a combination of wood and metal materials. Surrounding lush green fields are dotted with trees, enhancing the peaceful atmosphere.

Barn in Queenstown

4.99 out of 5 average rating, 85 reviews

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Outdoor spacesLocationDecor

Guest favourite

A serene outdoor area features four white Adirondack chairs arranged around a stone fire pit. A boat is docked nearby, with wooden piers extending into the calm water, surrounded by lush greenery and a clear blue sky.

Home in Newcomb

4.99 out of 5 average rating, 68 reviews

Saint Michaels Waterfront Home

This beautiful waterfront home sits just over the bridge entering St. Michaels. Two large bedrooms, two full bathrooms, and Two sofas make this a very spacious for a large amount of guests. 1 minute to St. Michaels, 7 minutes to Easton and 30 seconds (right around the corner) to The Oaks Wedding Resort. Lots to do including kayaking, paddle boarding, biking or just taking in the views and wildlife. Great restaurants and local shops within minutes from this house! ST-739-YOS

LocationValueAmenities

Top guest favourite

A sunlit sunroom features three comfortable armchairs arranged around a small table, offering expansive views of the water through large glass windows. Natural light floods the space, accentuating the serene atmosphere in this inviting seating area.

Home in Bozman

5 out of 5 average rating, 47 reviews

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Outdoor spacesLocationBiking

Top guest favourite

A scenic view of a spacious green lawn bordering a tranquil waterway. A white house is positioned near the water's edge, surrounded by trees and a clear blue sky. The peaceful setting is enhanced by the gentle reflection of the landscape in the water.

Home in Oxford

4.99 out of 5 average rating, 95 reviews

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

ValueLocationHospitality

Top guest favourite

A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in Saint Michaels

4.98 out of 5 average rating, 113 reviews

SM's Premier Rental Heated Pool (opens 4/3)

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Outdoor spacesLocationNearby