Vacation rentals with a kayak in Cecil County

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Top-rated kayak rentals in Cecil County

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Top guest favorite

A charming cottage exterior features a welcoming front entrance framed by large windows. Bright green siding is complemented by vibrant flowering plants and manicured lawns, creating a serene setting. A decorative compass rose is positioned above the door, enhancing the cottage's coastal charm.

Home in North East

4.96 out of 5 average rating, 46 reviews

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people. Nap in our secluded backyard gardens. The cottage includes water access, kayaks, bikes, and a SUP board. Explore the town of NE to shop and dine in the region's top restaurants. Minutes from Elk Neck State Park which offers hiking, fishing, bird watching & mountain biking. Visit historic Havre de Grace, Hollywood Casino, or relax and catch a sunset and the cool breeze coming off the North East River

Guest favorite

The exterior of a cozy cottage is visible, featuring a light-colored façade and a garage. Sunlight illuminates a patio area with an umbrella, surrounded by a grassy yard. Trees provide natural shade, and the waterfront can be seen in the distance under a partly cloudy sky.

Home in Betterton

4.93 out of 5 average rating, 14 reviews

Waterfront Chesapeake Bay Cottage walk to Beach

Lovely cozy cottage with big waterfront views on the Chesapeake Bay on 1/2 an acre. Walk to the public Beach in historic Betterton. Modern playground, tennis/pickle ball courts nearby. A 7 minute walk to a lovely, usually deserted public beach with great swimming. Enjoy ann outdoor shower under the blue skies post beach! A quick 15 minute ride to Chestertown, Washington College, Downrigging Weekend! Betterton is located quick 1 1/2 hour ride/ 80 miles from Washington DC & Philadelphia.

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Home in Havre de Grace

5 out of 5 average rating, 3 reviews

Comfortable and quiet 3-bedroom

This charming 3-bedroom, 2-bathroom home in historic Havre de Grace is the perfect mix of perfect location and relaxing getaway. Easily stroll to shopping, restaurants and nightlife in downtown Havre de Grace, or take a kayak down to the Susquehanna River. Three private bedrooms feature a king bed, queen bed, and twin bed. One bathroom has a tub-shower combo and the other has a stand-up shower. Kitchen has all major appliances and gadgets. Parking is free and plentiful. It doesn't get better!

Guest favorite

Two colorful kayaks rest on a sandy beach, facing a calm waterfront. The gentle waves ripple in the background, reflecting the soft hues of the sky during sunset. A wooden pier extends into the water, complementing the serene coastal scene.

Cottage in Charlestown

4.96 out of 5 average rating, 162 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

Superhost

A blue kayak is suspended from the wall in a garage, accompanied by two yellow paddles and a red life jacket. The concrete floor and wooden walls create a practical storage space for outdoor equipment.

Cabin in Elkton

4.74 out of 5 average rating, 47 reviews

Large Cabin w/ RiverView&Hot Tub

Escape to our spacious cabin with river view! Only 2-3 hours from NYC/DC. Secluded in nature, it's a perfect, peaceful getaway for couples & small families. Enjoy stunning views, tranquility, and nearby amenities such as restaurants, vineyards, horse riding, kayaking, and more. Soak in the hot tub under a canopy of stars, enjoy a peaceful evening around the fire pit, or play pool/air hockey/ping pong or board games in the game room. Relax and create lasting memories. Book your stay today!

Top guest favorite

An expansive wooden deck is feature prominently, equipped with several loungers and chairs. Potted flowers add color alongside the deck. Large glass doors provide access to the indoors, and views of the surrounding trees and water are visible in the background.

Home in Perryville

4.99 out of 5 average rating, 114 reviews

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Top guest favorite

A tranquil sunset casts golden hues over the calm waters of the Elk River. A boat glides through the reflective surface, leaving a gentle wake. The sky is filled with soft clouds, enhancing the serene atmosphere of the waterfront.

Cottage in Elkton

5 out of 5 average rating, 7 reviews

Rustic River Retreat

Take it easy at this unique and tranquil getaway. Part of a 3 unit home directly on the Elk River. Beautifully renovated 1 bedroom (queen) 1 bath guesthouse with 2 (full) bed sleeping loft. An additional sleeping area available upon request (additional fee). Enjoy beautiful scenery, sunsets, and wildlife from the deck. Fish and crab off the dock. Use available kayaks or bring your own. Close to Chesapeake City, North East, Elk Neck State Park, U of D, and tax free Delaware shopping.

Two adirondack chairs, one green and one red, are positioned on a grassy area overlooking a calm body of water. Trees frame the scene, offering a sense of privacy. The sky is dimmed, suggesting early evening light.

Vacation home in North East

4.91 out of 5 average rating, 69 reviews

Bonfire by the Creek

Relax in this cozy little home by the creek; fully furnished, beds freshly made; plenty of pillows & blankets, two TV's, and a fully-equipped kitchen. Be sure to take one of our kayaks out to explore the cove & creeks along the Elk River, then cookout on our propane grill & enjoy your dinner by the creek watching the wildlife- Eagles, Osprey, Heron, Ducks, Geese, & maybe even deer or a fox walking along the shoreline. After dinner, a bonfire is a great way to enjoy the evening!

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Home in Charlestown

4.89 out of 5 average rating, 37 reviews

The Sunset House

Spacious 5-bedroom, 3-bathroom home in Charlestown, MD, perfect for families and groups! Enjoy 2 king beds, 3 queen beds, a fully stocked kitchen, and a cozy outdoor entertaining area with a grill, fire pit (wood provided), and a relaxing hot tub. Just 1.5 blocks from the Chesapeake Bay, with kayaks and paddleboards available for your adventures. Plenty of games included for added fun. Ideal for your next getaway! Bringing a boat? Utilize the mooring while you stay!

Guest favorite

A spacious deck extends over the water, offering views of the calm river. A Maryland flag flutters gently in the breeze, and abundant greenery frames the scene. The serene environment is complemented by the subtle presence of a grassy area below.

Home in Perryville

4.93 out of 5 average rating, 214 reviews

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Top guest favorite

Four kayaks, two in vibrant colors and two neutral tones, are mounted on a gray wall within a garage space. A paddle is positioned above the kayaks, while a bicycle and a cooler sit on the floor, indicating a space for outdoor equipment.

Home in Charlestown

4.98 out of 5 average rating, 47 reviews

Catching Sunsets on the Bay

Come and enjoy this brand new home, built for making memories on the Chesapeake Bay! Our spacious 3 bedroom, 2.5 bath is perfect for your next getaway. Our cozy, yet modern home is within feet of the Northeast River where you can take in the beautiful views, go kayaking, swimming or boating, or take a 12 minute drive to the new Great Wolf Lodge! Our home is perfect for couples or families as we have games, toys, and a pack n play if needed!