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Vacation rentals with a kayak in Southern Maryland

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Southern Maryland

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

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A wooden dock extends into calm waters, framed by lush greenery. Two kayaks are secured to the side of the dock, and an expansive sky filled with soft clouds reflects over the serene surface of the creek, creating a peaceful outdoor scene.

4.93 out of 5 average rating, 213 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Top guest favorite

A peaceful sleeping area features a neatly made bed with floral-patterned bedding in blue tones. A wooden nightstand holds a book and a small plant, while a warm light illuminates the wall, creating a cozy ambiance.

5 out of 5 average rating, 380 reviews

Treetop Loft Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons and Calvert Cliffs. Totally private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen. Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Choose to stay in or adventure out. NOTE: Smoke-free & peanut-free property as we are allergic to both. Scent Free in your space. Air Purifier. We only use Melaluca cleaning products

A gravel path leads through a wooded area to a serene water body. Three green kayaks are positioned alongside the path, ready for use. Sunlight filters through the trees, creating a calming natural setting.

Home in Montross

4.98 out of 5 average rating, 114 reviews

3N PROMO | Waterfront | Beach+Gamerm+Kayak/Pddlbd

*Ask about our 3N+ promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet Whether you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples. Relax - Star Gaze - Kayaks - Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

Top guest favorite

An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.

Home in Cobb Island

4.99 out of 5 average rating, 105 reviews

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

Top guest favorite

A serene view of the river at sunset, showcasing vibrant hues of orange and pink reflecting on the water's surface. Silhouetted trees frame the scene, and a quiet dock extends into the water, creating a peaceful atmosphere in the rural setting.

Guest suite in Warsaw

4.98 out of 5 average rating, 141 reviews

The Osprey Nest: Rappahannock Riverfront Suite

Sunny, private 2nd floor suite at the river's edge features panoramic views of the Rappahannock and surrounding farmland. Take in fiery sunsets, sunrises, starry skies, eagles, ospreys and more. Swim, fish, explore waterways by kayak, or bike in tranquil, rural surroundings. Morning coffee on the balcony with the songbirds is a treat, and the riverfront deck, surrounded by trees is sublime. Restaurants, historic sites, hiking, fossil hunting, wineries, antiques & more are a short car ride away.

Top guest favorite

The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.

Home in Shady Side

5 out of 5 average rating, 181 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Top guest favorite

Guest suite in Lusby

4.98 out of 5 average rating, 355 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.

Cottage in Leonardtown

4.96 out of 5 average rating, 215 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Top guest favorite

The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.

Apartment in Lexington Park

4.97 out of 5 average rating, 582 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Top guest favorite

A single-story house is shown with blue siding and white trim, featuring a prominent brick chimney and a welcoming pink door. Large windows provide ample natural light. A grassy area surrounds the home, with trees adding greenery in the background.

Home in Piney Point

5 out of 5 average rating, 122 reviews

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Top guest favorite

A spacious cottage is viewed from the water, elevated on a tiered wooden deck. White railings and steps lead to the outdoor areas. Lush greenery surrounds the property, with a blue slide visible on the lower deck beside the water's edge.

Home in Colonial Beach

5 out of 5 average rating, 114 reviews

Waterfront Cottage in Colonial Beach at Placid Bay

Luxury Cottage with private water views full of natural wildlife. You will love the open floor plan with a chef's kitchen stocked with All the essentials including beverages and coffee. Sleep late with private bedrooms that include luxurious bedding Enjoy the expansive outdoor space complete with Patio, Pergola, Fire Pit, and large deck with outdoor kitchen. Walk down to the 28ft foot dock where you can fish, relax in the sun or take the Kayaks for a ride Close to DC and NOVA

Top guest favorite

The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.

5 out of 5 average rating, 149 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

*Heated pool open to Nov 2* Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool (May–October) with amazing river views. The estate also hosts weddings and events for up to 100 guests (additional event fee applies).

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Southern Maryland kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

A corner of the studio is equipped with a kayak, accompanied by life jackets and storage boxes. A bicycle is also visible, providing options for outdoor activities and exploration.

Home in Piney Point

5 out of 5 average rating, 33 reviews

Waterfront Studio | Bikes & Kayaks | Beach Access

Top guest favorite

A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.

Home in Woolford

4.93 out of 5 average rating, 161 reviews

Waterfront Getaway with Dock

An aerial view captures a charming single-story home nestled among lush greenery, with a panoramic view of Mattox Creek extending to the Potomac. The well-maintained landscaping and surrounding trees create a peaceful setting, highlighting the home's proximity to the water.

Home in Colonial Beach

4.89 out of 5 average rating, 65 reviews

Waterfront Home w/ Private Dock!

Top guest favorite

A charming riverfront home is framed by lush greenery and colorful flowerpots. A welcoming pathway leads to the front door, flanked by well-maintained garden beds. The expansive porch invites relaxation, with captivating views of the serene landscape visible in the distance.

Home in Montross

4.95 out of 5 average rating, 20 reviews

New Private Beachfront panoramic view every window

A serene view showcases a dock extending into calm waters at sunset. Silhouetted Adirondack chairs are positioned facing the horizon, where the sun dips below the water, casting a warm glow across the sky and reflecting on the tranquil surface.

Home in Lottsburg

4.96 out of 5 average rating, 53 reviews

Waterfront Escape!

Top guest favorite

A circle of bright blue Adirondack chairs surrounds a metal fire pit, set on a pebbled area with expansive views of the Chesapeake Bay. The calm water reflects a colorful sky at sunset, enhancing the serene atmosphere.

Home in Reedville

5 out of 5 average rating, 75 reviews

The Haven On The Chesapeake Bay

A serene scene captures a lone goose standing on a wooden dock. The still water reflects the dock's structure and posts, creating a mirrored effect. The surrounding area features additional posts rising from the water, contributing to a peaceful waterfront atmosphere.

Home in Tall Timbers

4.89 out of 5 average rating, 127 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

A modern home with a striking design is visible, showcasing large floor-to-ceiling windows that invite natural light. The wooden deck surrounds a clear pool, with a separate spa area nearby, blending seamlessly with the outdoor space and landscape.

Home in Stafford

4.9 out of 5 average rating, 108 reviews

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks

Cottage rentals with a kayak

Top guest favorite

An inviting deck features a turquoise picnic table and comfortable seating with floral cushions, offering views of Cod Creek. Large windows span the cottage facade, allowing natural light to fill the interior. Surrounding trees provide a serene backdrop.

Cottage in Heathsville

4.88 out of 5 average rating, 123 reviews

Cottage with a view!

A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.

Cottage in Deale

4.95 out of 5 average rating, 167 reviews

Chesapeake Bay Cottage

A covered deck offers seating with wicker chairs and colorful cushions overlooking the calm waters of the Chesapeake Bay. The decking is made of warm-colored wood, and a gentle view of the shoreline can be seen in the distance, enhancing the serene atmosphere.

Cottage in Reedville

4.88 out of 5 average rating, 221 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

A remodeled cottage is set amidst a green lawn, featuring a spacious screened front porch and surrounded by trees. The building showcases a classic design with a dark exterior and a contrasting light roof, under a clear blue sky.

Cottage in Warsaw

4.91 out of 5 average rating, 127 reviews

Modern 2 Bdrm Cottage in Historic River Community

Top guest favorite

A waterfront cottage is set against a backdrop of lush greenery, with a stone wall bordering the water. The well-maintained lawn extends towards the river, and the cottage features a covered patio, inviting outdoor seating, and a surrounding cluster of trees.

Cottage in Cobb Island

4.96 out of 5 average rating, 71 reviews

Where Eagles Soar *Stunning Waterfront Views*

A charming blue cottage features a spacious front deck with wooden railings and steps leading up to the entrance. Large windows allow for ample natural light, while the surrounding grass lawn and trees enhance the outdoor setting.

Cottage in Colonial Beach

4.84 out of 5 average rating, 110 reviews

Bungalow Private Beach & Dock Colonial Beach Water

A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.

Cottage in Montross

4.93 out of 5 average rating, 100 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 165 reviews

Waterfront Chesapeake Bay Sunrises & Private PIER!

Cabin rentals with a kayak

A sleek Scandinavian micro home made of spruce is set against a backdrop of colorful autumn foliage. Large windows provide ample natural light, while a patio area features comfortable seating and dining options. The surrounding lawn is well-maintained, creating an inviting outdoor space.

Cabin in Indian Head

4.97 out of 5 average rating, 33 reviews

*Private Waterfront Retreat w/3 Cabins Close to DC

Cabin in Saint Michaels

4.99 out of 5 average rating, 115 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

A sunlit deck extends alongside the cottage, featuring smooth wooden planks. Two chairs and a small table are positioned invitingly near the edge, with tall trees providing shade and a view of the bay beyond.

Cabin in Reedville

4.79 out of 5 average rating, 29 reviews

"Elderberries" Chesapeake Bayfront Cottage

A log cabin with a rustic exterior is surrounded by lush greenery. The wraparound porch features a wooden railing and an American flag hangs proudly. A detached garage is visible in the background, and the property is set against a peaceful lake.

Cabin in Lancaster

4.91 out of 5 average rating, 66 reviews

Riverside R&R: Cabin, Dock, Kayak & Game Arcade

An aerial view showcases the property surrounded by tall trees, with a clear path leading to a waterfront area. The serene water reflects the sunlight, while the landscape features a mix of greenery and open space, highlighting the tranquility of the setting.

4.96 out of 5 average rating, 74 reviews

Pizza Friday

A kayaker is seen navigating calm waters, with gentle ripples surrounding the red kayak. A shoreline of trees and grass transitions into a distant view of a white house along the bank, framed by blue skies.

Cabin in Saint Michaels

4.75 out of 5 average rating, 81 reviews

Cottage #4 Chesapeake Blue down the drive way.

Top guest favorite

A charming black exterior cottage is surrounded by autumn foliage, featuring a welcoming front porch with steps leading to the entrance. Flower boxes adorn the windows, while a small deck is visible to one side, adding to the inviting outdoor space.

Cabin in Montross

4.97 out of 5 average rating, 30 reviews

Camp Heron : Waterfront Cabin on the Potomac

Top guest favorite

A serene lakeside view features a wooden dock extending into the calm water, flanked by greenery. Two kayaks are displayed on a rack, while a fire pit with seating is positioned nearby. A safety notice is visible, ensuring guest awareness.

4.98 out of 5 average rating, 97 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

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