Vacation rentals with a kayak in Charles County

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Top-rated kayak rentals in Charles County

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Guest favorite

A spacious wooden deck is showcased, extending from the house and featuring several outdoor chairs arranged around a table. The sun sets in the background, casting a warm glow over the grassy yard and the nearby water, enhancing the serene ambiance.

Home in Leonardtown

4.95 out of 5 average rating, 76 reviews

The River House: A private waterfront oasis…

Fall brings apple picking, oysters, bald eagles and great weather! This private waterfront retreat offers panoramic water views of the Potomac River and sits at the mouth of Breton Bay. At the end of the road and occupying two acres, the property is a private oasis of year-round natural beauty. You’ll have 650’ of waterfront to yourself to lounge at the waterside tiki-bar deck, on the screened-in porch, on the house deck, in the yard or on the hammock. Kayak, canoe, chill however you like. Bliss

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!

Guest favorite

A wooden dock extends into calm waters, showcasing a boat moored at the end. The serene surface reflects the pastel colors of the sky during dusk. Wooden posts line the edges of the dock, enhancing the tranquil setting.

Home in Newburg

4.91 out of 5 average rating, 117 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

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*

Escape to our tranquil waterfront cottage on Cobb Island, just a 1 hour and 20 minute drive away from the bustling city of NOVA and Washington DC. This hidden gem offers a perfect refuge for those seeking a peaceful retreat, a romantic getaway, a girls' trip, a remote workspace, or a solo getaway to unwind and recharge. You will undoubtedly want to return again and again You are welcome to bring your boat as their is ample space in the large wrap-around driveway suitable for parking.

Guest favorite

A spacious dining area is surrounded by large floor-to-ceiling windows, allowing natural light and views of the outdoors. A long wooden table is accompanied by modern chairs and is adorned with plants, enhancing the inviting atmosphere of the space.

Home in Stafford

4.9 out of 5 average rating, 108 reviews

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks

This property sits on the edge of a bluff overlooking the Potomac River and boasts stunning views, both from within and around the home, perfect for bird watching (eagles/osprey), fishing or just relaxing and soaking in nature, just minutes from DC! PLEASE READ CAREFULLY: The pool and spa are CLOSED from LABOR DAY through MEMORIAL DAY. The official open season for pool and spa is between Memorial Day and Labor Day, please confirm availability (if requesting) outside of standard season.

Guest favorite

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!

Gorgeous views of Mattox Creek which runs into the Potomac from the 100' private pier. Swim or fish straight from dock; bring your boat/kayaks! 3 BR/3 BA stepless ranch w/ tons of natural light. Updated Kitchen w/ newer appliances, cabinets & plenty of counter space. Separate Butler's Pantry. Wood fireplace & pellet stove. Pets welcome! 45 min to F'burg/Tappahannock. Private neighborhood. Minutes to downtown Colonial Beach shopping/dining. Free Internet & Utilities w/ up to 30 day stay.

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

Guest favorite

The bathroom features a vintage cast-iron tub positioned against textured white tiles. A mosaic floor adds character. Natural light enters through a window, and a small table is visible in the corner. Fixtures include a handheld shower and wall-mounted water controls.

Bungalow in Colonial Beach

4.9 out of 5 average rating, 29 reviews

“On Point” - Art Deco Cottage on the Point

Kick back and relax in style. The covered porch welcomes you with 1930’s spring chairs, ceiling fan, and locust wood tables made from the original foundation. For bath-lovers, the 1930s cast-iron tub (known to keep hot water hot) will be calling your name, hugging you as soon as you get in. The waterfall shower, hand-held shower, and rotating faucet will accommodate every guest. The bedroom offers a cooling mattress, adjustable bed, mood lighting, TV, and extra storage.

Top guest favorite

An open concept living area features a combination of seating, including two armchairs and a side table. A dining area with a striking blue rug and wooden chairs is visible in the background, alongside a well-lit kitchen area with modern appliances.

Guesthouse in Owings

4.95 out of 5 average rating, 111 reviews

Patuxent River View

🌊 Nestled near North Beach, Herrington Harbor, Herrington on the Bay, and Chesapeake Beach, this serene guest house offers a peaceful escape for travelers of all kinds—whether you’re exploring local sights, reconnecting with nature, visiting family, or just passing through. Guests enjoy thoughtful amenities at no extra cost: a fully stocked kitchen, complimentary coffee and tea, high-speed WiFi, a pool and gazebo, and more comforts to make you feel right at home.

Superhost

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

Furnished, 2 bedrooms (2 queen) & one bath with private dock privileges for fishing crabbing & boating. Water view from the deck & private beach access steps away. 3 Blocks to Town, Walk to restaurants, playground & casino. Sit on the deck that wraps around the home & overlooks the water. Large grass yard to play games , cookout, or sit by the fire. There is a full kitchen & washer/dryer. Just renovated. Golf cart available to rent. Linens included.

Guest favorite

A solitary kayak glides across calm waters, silhouetted against a vibrant sunset. The sky is painted in shades of orange and blue, with wispy clouds reflecting in the water's surface, creating a serene atmosphere.

Home in Newburg

4.91 out of 5 average rating, 82 reviews

Peaceful waterfront home, 1-hour from DC

Beautiful home with stunning sunset views on the lower Potomac River. Home features a private pier, fire pit, theater room, and play area for kids! Only 1 hour from DC, 90 mins from Richmond. Easily accessible from anywhere in the DMV area. Full kitchen, and large screened in back porch. This is a vacation home-come true.

Guest favorite

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

Escape to our serene 4-acre retreat overlooking the Potomac River, just a 40-minute drive from Washington, D.C. This property features a fully refurbished 3-bedroom cabin and a charming tiny house, offering a perfect blend of rustic charm and modern amenities for families and groups seeking tranquility and adventure