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 two-story blue house is set against a clear sky, offering a welcoming facade. The driveway leads to a spacious outdoor area, featuring a grassy yard and seating arrangements near the water. Leafless trees frame the property, emphasizing the natural surroundings.
Home in North East
5 out of 5 average rating, 19 reviews

Riverfront Haven @ Hances Point

Relax with the whole family at this peaceful, riverside retreat! Enjoy comfortable, open-concept living in this spacious indoor/outdoor setting. You are located back a private drive, with plenty of outdoor space to enjoy the water, yard games, fire pit and kayaks, and frequent bald eagles overhead. Plenty of parking for your whole family or group. Beautifully appointed kitchen, large living area, screened in porch, and two 75" TV's. Convenient to local shops, restaurants, parks and fishing.

Superhost
A serene waterfront scene captures a still lake at sunset, with silhouettes of dock pilings and boats reflected in calm waters. The sky transitions from soft orange to deep blue, creating a tranquil atmosphere that invites relaxation.
Home in Perryville
5 out of 5 average rating, 3 reviews

Waldins Chesapeake

Winter sunrises or summer water fun, Waldins is a beautiful retreat any time of year. With the million dollar view just out back there is no need to go anywhere else. Recently renovated the house is immaculate. State of the art entertainment system and modern kitchen provide all the accouterments necessary for a comfortable stay. On the water without the typical "beach house" decor, this place is one of a kind . Bring your water toys, dock at our 160' pier and maximize all the area has to offer

Guest favorite
A front porch offers a view of the expansive Chesapeake Bay. Two red cushioned chairs are positioned around a small round table. Lush greenery and a pathway lead towards the waterfront, with the horizon visible in the distance under a clear blue sky.
Home in Betterton
4.97 out of 5 average rating, 30 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.

Guest favorite
A spacious dining area features a large rectangular table surrounded by metal chairs. Natural light flows in through the windows, illuminating the room. A decorative globe and an open shelving unit are present, adding character to the space. The flooring is a light wood, contributing to a warm atmosphere.
Home in Havre de Grace
4.92 out of 5 average rating, 12 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
Cottage in Charlestown
4.95 out of 5 average rating, 215 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

Top guest favorite
A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.
Home in Perryville
4.99 out of 5 average rating, 133 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!

Guest favorite
Home in Elkton
4.94 out of 5 average rating, 16 reviews

A Waterfront Christmas for 2025 is still available

Now Booking Fall 2025 and Summer 2026 going quick! The incredible 4-bed 2-bath water-facing home is the ultimate getaway Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with a $125 docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2) Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - mid May** We do not have a separate stand alone hot tub

Guest favorite
The kitchen features light wood flooring and a combination of gray cabinetry and white appliances. Large windows allow natural light to fill the space. A small island with three stools provides casual seating, while a ceiling fan enhances airflow.
Home in Charlestown
4.93 out of 5 average rating, 60 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 panoramic view showcases a cozy two-story house set against a serene waterfront backdrop. Colorful autumn foliage lines the shore, reflecting vibrant hues in the calm water. A grassy area with a small beach adds to the inviting outdoor space, perfect for relaxation.
Home in Perryville
4.93 out of 5 average rating, 224 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.

Guest favorite
A spacious living area is highlighted by large windows offering views of the sunset. Comfortable seating includes a sectional sofa and a pair of chairs, positioned around a decorative rug. A flat-screen television and an electric fireplace complete the welcoming ambiance.
Home in Charlestown
4.98 out of 5 average rating, 59 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!

Guest favorite
A serene waterfront view is presented at sunset, with calm waters reflecting warm hues of orange and pink. Silhouettes of boats are anchored along wooden docks, and gentle ripples add a touch of tranquility to the scene.
Home in Earleville
4.92 out of 5 average rating, 176 reviews

Cozy 4 BR 3 BA Near Chesapeake City

Peaceful, cozy modern cottage with many amenities in a water-oriented community along the Bohemia River. Just minutes from Chesapeake City and located across the street from the water. Our house is perfect for family vacations, tranquil retreats, girl/guy getaways, weddings, wedding guests. Two queen master BR’s w/private baths on the first floor, second floor has one larger BR w/twins and smaller BR w/daybed +trundle and shared bathroom.

Guest favorite
A well-lit wooden dock extends over the calm water, leading to a two-story house surrounded by trees. The evening sky is adorned with scattered clouds, and reflections of lights shimmer on the water's surface, creating a peaceful ambiance.
Home in Perryville
4.88 out of 5 average rating, 16 reviews

Chesapeake Waterfront Vacation Rental with Dock

Relax at this peaceful waterfront vacation rental on the upper Chesapeake. 2 King beds, a Queen, a large Bunk bed, and a Day bed: 5 BRs, 2 Bath with spacious deck. 100 foot dock (has water and electric) with lots of room for water activities and fun in the sun. Tie off your boat or jet skis. 2 kayaks provided. Very clean and comfy. Linens and Kitchen amenities provided. All four 2nd floor bedrooms have smart TVs as does the living room.

Popular amenities for Cecil County kayak rentals