Vacation rentals with a kayak in Cecil County

5.0 out of 5 average rating, 30 reviews

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

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.

Outdoor spacesLocationKitchen

Superhost

Home in Havre de Grace

4.82 out of 5 average rating, 17 reviews

Charming Havre de Grace Home Walk to Downtown

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!

Outdoor spacesLocationCondition

4.94 out of 5 average rating, 85 reviews

Home in Charlestown

The Sunset House-Hot Tub-Sauna

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! Brand new sauna on site! Bringing a boat? Utilize the mooring while you stay!

Outdoor spacesLocationQuiet

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.

4.96 out of 5 average rating, 167 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!

LocationOutdoor spacesNearby

4.95 out of 5 average rating, 19 reviews

A clear, inviting saltwater pool is framed by textured ivory paver stones. Lush greenery and ornamental shrubs line the pool area, providing a tranquil atmosphere. The expansive water view extends beyond the pool, under a bright blue sky adorned with fluffy clouds.

Home in Elkton

Breathtaking Waterfront w/pool and private dock

Only 1 week left for Summer 2026! Fall dates still available. This incredible 4-bed 2-bath water-facing home is the ultimate getaway. Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - May** We do not have a separate stand alone hot tub. 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)

Outdoor spacesLocationRiver

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.

4.9 out of 5 average rating, 10 reviews

Waldins Chesapeake

Waldins is a waterfront escape for any season, with a million-dollar view right outside your door. Recently renovated, the home blends modern comfort with distinctive Southwest style. Enjoy the well appointed and updated kitchen, entertainment system, and inviting spaces inside and out. Bring the water toys and tie up at the private 160-foot pier. Have coffee at sunrise, visit nearby waterfront dining and bars, or relax on the veranda watching eagles and passing boats.

LocationOutdoor spacesSleep quality

4.96 out of 5 average rating, 288 reviews

Cottage in Charlestown

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & 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...

ValueLocationView

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.

4.92 out of 5 average rating, 247 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.

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4.96 out of 5 average rating, 106 reviews

Two vibrant blue adirondack chairs are positioned beside a small, round table, creating an inviting outdoor seating area. In the background, the tranquil waters of the Bohemia River reflect the warm hues of sunset, framed by lush trees and marina boats.

Cottage in Earleville

The Bohemia Charmer

Take it easy at this unique and tranquil getaway. In the Hack's Point Community, on the shores of the Bohemia River, this home will give you plenty of opportunities to relax, no matter the season. This home has the closest proximity to the community beach and pier, and it also exudes historic charm with a stunning 2-story fireplace, hardwood & stone flooring, and built-ins. ***There is no guest access to the pier for storage or day-use of boats***

LocationOutdoor spacesSleep quality

4.99 out of 5 average rating, 80 reviews

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

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!

ValueLocationFamily

4.92 out of 5 average rating, 183 reviews

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

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.

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