Vacation rentals with a kayak in Cecil County

4.71 out of 5 average rating, 49 reviews

A dining area is set with neatly arranged plates, glasses, and silverware, surrounded by wooden chairs. The room features exposed wooden beams, a brick fireplace, and large windows offering views of the serene river landscape. Natural light fills the space, enhancing its inviting atmosphere.

Cabin in Elkton

Large Cabin w/ RiverView&Hot Tub

KatieRating, 5 stars3 months ago

This cottage was the perfect respite for my family. The big panoramic window that looked out over the water was perfect. The house was so comfortable and the hosts were very responsive. Highly recommend a stay here. There isn’t a lot to do in the immediate area, but the university of Delaware was 20 minutes away and Baltimore an hour south. It was a perfect house for a long weekend getaway.

4.94 out of 5 average rating, 35 reviews

A scenic view showcases a waterfront property surrounded by lush greenery. A wooden deck extends toward the water, alongside a grassy area. An American flag gently flutters in the breeze, while a path leads to the entrance of the house with large windows facing the bay.

Cabin in North East

Sunset Bay Waterfront cottage on Chesapeake Bay

JohnRating, 5 stars1 month ago

This was the second year I stayed here for four days. Bob is wonderful in his quick responses, helpful information about the area (tells me where the eagles are nesting each year as he knows I come to see the birds), and makes me feel so welcomed. Had the kayaks out and ready, had a fire really to light in the fire ring. The house is very loved by Bob and he is family, and it is so comfortable, clean, and has everything and more that I needed. All around, a great host and a great house in a great setting!

5 out of 5 average rating, 7 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.

4.96 out of 5 average rating, 53 reviews

The cottage's exterior features a welcoming façade with a green color scheme. A compass motif sits above the entrance. Surrounding gardens include various plants and shrubs, with a stone pathway leading to the front door. Large windows allow natural light into the space.

Home in North East

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people with 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, and mountain biking. Visit the lighthouse, Havre de Grace, Hollywood Casino, or relax & catch a sunset with a cool breeze coming off the North East River.

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

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

5 out of 5 average rating, 3 reviews

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

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!

4.94 out of 5 average rating, 175 reviews

An outdoor seating area features comfortable gray cushions and a dark wooden coffee table, positioned on a deck overlooking a serene waterfront. The vibrant sunset casts warm hues across the sky, reflecting on the calm water, creating a tranquil atmosphere.

Cottage in Charlestown

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

4.99 out of 5 average rating, 121 reviews

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

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!

4.91 out of 5 average rating, 46 reviews

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

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!

4.93 out of 5 average rating, 218 reviews

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

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.

4.98 out of 5 average rating, 51 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!

4.92 out of 5 average rating, 165 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.

Vacation rentals for every style

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Popular amenities for Cecil County kayak rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

House rentals with a kayak

4.95 out of 5 average rating, 141 reviews

An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.

Home in Riviera Beach

Waterfront Cheerful 5 home

LeslieRating, 5 stars3 weeks ago

We were in town for a wedding and this home was as described and was perfect for our family of 8 that stayed here. The neighborhood was quiet and peaceful. I wish we had time to enjoy the views from the lake. John was a great host and communicated with us throughout our stay. I would recommend this home to anyone who is looking to stay in the Riviera Beach or Pasadena area. It was close to everything we needed during our stay including the airport.

5 out of 5 average rating, 55 reviews

Home in Abingdon

Rogue Wave River Retreat

JoyRating, 5 stars1 week ago

Absolutely amazing place. Right on the water, several decks to sit out and enjoy. Quiet location. Beautiful kitchen, comfy living space, bonus TV room in the basement was great for kids. Nice-sized bedrooms, impeccably clean and with everything you need. Stayed here for a Ripken tournament; was 15 minutes away from the facility and so enjoyable when we had downtime from our games. Can't recommend more highly; wish we could have stayed longer.

4.93 out of 5 average rating, 30 reviews

An expansive deck with a wooden dining table is surrounded by several chairs. Lush greenery provides a natural backdrop, and a winding path leads down toward the waterfront, offering a view of the serene Chester River.

Home in Millington

Lark's Nest on the Chester River

LaurelRating, 5 stars5 months ago

This was our second time at Leone's beautiful spot on the Chester River and it did not disappoint! It's such a beautiful place and beautiful location -- we absolutely love it!! Thank you Leone!!!

5 out of 5 average rating, 31 reviews

An inviting living area features a blend of textures and colors, including a plush rug, a vibrant green sofa, and orange accent chairs. Large windows provide ample natural light, while a ceiling fan and spiral staircase add to the airy atmosphere. Decorative elements suggest a beach-inspired theme.

Home in Rock Hall

1-Particular Harbor: A Coastal Oasis!

FrannieRating, 5 starstoday

We had an amazing weekend and Gregory’s home was perfect. So clean and well equipped. Gregory thought of everything!! Highly recommend ⭐️⭐️⭐️⭐️⭐️

4.94 out of 5 average rating, 72 reviews

Home in Chestertown

Waterfront w/ Hot Tub + Dock | Harbor View Haven

AiyanaRating, 5 stars1 week ago

A group of us went to Chestertown, MD for Memorial Day weekend. The house was exactly as described and the host was friendly. There was a full kitchen with everything you’d need and plenty of linen and towels for everyone. I think the space was perfect and had so much to offer for a great price.

5 out of 5 average rating, 38 reviews

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

Water Views in Rock Hall

CorrieRating, 5 stars3 weeks ago

We had a wonderful stay at this beautiful house. Everything was clean and didn't show signs of use. The house was comfortable and in a beautiful location with amazing views. We loved the wonderful screened in outdoor dining area, bikes, watersport items, comfortable beds, games and easy and clear information. We would love to stay here again.

4.96 out of 5 average rating, 108 reviews

A serene sunset over the water displays vibrant hues of orange and pink, framed by gentle clouds. Silhouettes of beach chairs are visible in the foreground, inviting relaxation as the day transitions to evening.

Home in Salem

Beachfront Sunsets on the Water at Oakwood Beach

AdriannaRating, 5 stars1 month ago

This house was perfect for my sister’s bachelorette weekend! Jahneva was a great host, and I would stay here again if I’m back in the area!

4.99 out of 5 average rating, 150 reviews

A newly constructed home is situated near a serene pond, surrounded by blooming cherry trees. A gazebo stands adjacent to the water, complete with seating. The house features multiple decks with views of the landscaping and tranquil water, enhancing the peaceful atmosphere of the location.

Home in Holtwood

Swan Lake

LindaRating, 5 stars1 week ago

We have stayed at many AirBBs, this one was by far our favorite for our family vacation. Absolutely beautiful and the grounds were amazing. We were happy with everything. Everything was exactly as represented. We will definitely be back

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Cottage rentals with a kayak

The exterior of the cottage showcases a stone facade with a welcoming front entrance, framed by a wooden door. Lush green grass surrounds the home, complemented by ornamental shrubs and a flowering plant at the base of the steps. An American flag adds a touch of character.

Cottage in Wrightsville

4.82 out of 5 average rating, 90 reviews

Private Hot Tub at Cozy Wrightsville Cottage!

JanetRating, 5 stars2 weeks ago

Beautiful setting along the river. Charming decorations, which reminded visitors of the history of the building, a one room schoolhouse. The combo lock on the door did not work, but the issue was resolved immediately by the host. No other issues.

5 out of 5 average rating, 43 reviews

Two kayaks in vibrant green and bright blue are positioned at the lower deck, alongside two paddle boards that rest in an organized manner. A prominent mermaid statue is displayed in the background, adding a coastal charm to the waterfront setting.

Cottage in Essex

The Little House of Rockaway Beach, Maryland

CasandraRating, 5 stars2 months ago

There are no words to express our gratitude 🙏 !! We absolutely loved “the little house” on rockaway beach…It was truly a healing home…we went to Baltimore for my husband’s ankle replacement surgery..this home could not be any more perfect for us…we can’t wait to come back….thank you again and again Brent & Jennifer!! ❤️❤️❤️❤️❤️❤️Casandra Amazing sunrises on the Potomac, close to Baltimore/Washington DC/Annapolis &more, nestled in the charming Rockaway Beach in Essex… The Little House is a comfortable & welcoming retreat. Me on my knee scooter, rolling into the kitchen, bedroom, bathroom and shower. Brent & Jennifer are Super Hosts for good reason, their warm hospitality and impeccable curated beach cottage make for the perfect Maryland getaway, no matter the season. We’ll be back! Scott 😍😍

5 out of 5 average rating, 6 reviews

A cozy seating area features four wooden Adirondack chairs arranged around a stone fire pit, set beside a snow-covered creek. The scene includes bare trees lining the creek and a hint of sunlight illuminating the winter landscape.

Cottage in Delta

The Cabin at Muddy Creek

SarahRating, 5 stars6 months ago

This was the most beautiful setting for Thanksgiving! The house was so cozy, and the property was unreal. We loved hiking, playing on the swing, watching the eagles, and fishing for Trout. Hot tub was a nice touch, too! Thanks so much for everything- we can’t recommend enough! 5 stars!

4.97 out of 5 average rating, 175 reviews

A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.

Cottage in Pasadena

Ft. Smallwood Overlook. Waterfront with Kayaks!

EmilyRating, 5 stars2 weeks ago

Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !

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Cabin rentals with a kayak

4.94 out of 5 average rating, 35 reviews

The elevated house is set among trees, featuring a spacious deck with multiple chairs and a table. Large windows are visible on the front, allowing natural light inside. The underside of the deck shows storage for various outdoor equipment, indicating a functional outdoor space.

Cabin in North East

Sunset Bay Waterfront cottage on Chesapeake Bay

JohnRating, 5 stars1 month ago

This was the second year I stayed here for four days. Bob is wonderful in his quick responses, helpful information about the area (tells me where the eagles are nesting each year as he knows I come to see the birds), and makes me feel so welcomed. Had the kayaks out and ready, had a fire really to light in the fire ring. The house is very loved by Bob and he is family, and it is so comfortable, clean, and has everything and more that I needed. All around, a great host and a great house in a great setting!

4.96 out of 5 average rating, 91 reviews

A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.

Cabin in Worton

Cabin on the Creek ~ Kayaks and Fire Pit

RachelRating, 5 stars1 week ago

We loved being in the woods and right by the river. Access to kayaks was a big draw. The home was comfortable and had everything we needed. We also loved being just a quick drive to Chestertown.

4.71 out of 5 average rating, 49 reviews

Cabin in Elkton

Large Cabin w/ RiverView&Hot Tub

KatieRating, 5 stars3 months ago

This cottage was the perfect respite for my family. The big panoramic window that looked out over the water was perfect. The house was so comfortable and the hosts were very responsive. Highly recommend a stay here. There isn’t a lot to do in the immediate area, but the university of Delaware was 20 minutes away and Baltimore an hour south. It was a perfect house for a long weekend getaway.