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Vacation rentals with a kayak in Calvert County

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Top-rated kayak rentals in Calvert County

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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.

4.92 out of 5 average rating, 216 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 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, 100 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

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, 383 reviews

Treetop Loft Retreat w/ Private Beach Access

Choose to stay in or adventure out: Experience our tucked-away loft 5 mins from beaches, 10 mins to Solomons & Calvert Cliffs. Totally private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. Enjoy fast Wi-Fi, a 40" Smart TV, a cozy queen bed w/ heated mattress pad, and fireplace. NOTE: Smoke-free & peanut-free property as we are allergic to both. Scent Free in your space. Air Purifier. Melaluca cleaning products

The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.

4.99 out of 5 average rating, 227 reviews

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

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, 153 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** 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 with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Top guest favorite

The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.

Home in Solomons

5 out of 5 average rating, 104 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

Home in Saint Leonard

4.89 out of 5 average rating, 133 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Top guest favorite

Guest suite in Lusby

4.98 out of 5 average rating, 356 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🥰

Top guest favorite

A two-story house features gray siding with white trim and a balcony accessed by stairs. An umbrella is positioned over the outdoor seating area, providing shade. Large windows illuminate the space, and a comfortable railing surrounds the deck, offering a peaceful setting.

Guest suite in Tilghman Island

4.97 out of 5 average rating, 159 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

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

4.92 out of 5 average rating, 115 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.

Top guest favorite

The exterior of a renovated beach house is depicted, featuring a wide entrance with steps leading to a spacious deck. The deck is furnished with a dining set and a shaded lounge area, while greenery surrounds the property, enhancing its tranquil setting.

5 out of 5 average rating, 201 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Top guest favorite

An entryway leads through tall grasses and dunes to a sandy beach covered with colorful umbrellas. The clear blue sky and calm water create a serene setting, while beachgoers enjoy the day in the distance.

Guesthouse in Saint Leonard

4.97 out of 5 average rating, 116 reviews

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.

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Quaint homes, peaceful surroundings

Popular amenities for Calvert County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Adirondack chairs are arranged on a grassy area facing the water. The sun is setting, casting a warm glow over the bay, with soft reflections visible on the surface. Trees provide shade, enhancing the serene outdoor setting.

Home in North Beach

4.94 out of 5 average rating, 81 reviews

A Little Piece of Paradise - Waterfront Home

Top guest favorite

A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.

Home in Mechanicsville

5 out of 5 average rating, 85 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

A charming two-story home is set against a clear blue sky, featuring a white exterior and a welcoming front pathway made of stone. Lush green grass surrounds the house, complemented by a white picket fence and well-maintained landscaping.

Home in Solomons

4.92 out of 5 average rating, 112 reviews

Roomy 6 bedroom home in the heart of Solomons, MD

Home in Saint Leonard

4.93 out of 5 average rating, 57 reviews

Lux Family Bay 5BR: GameRm, MovieRm, Kayak, Beach

Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.

4.98 out of 5 average rating, 99 reviews

Waterfront with sweeping bay view & private beach

Top guest favorite

The exterior of the home is shown, featuring a light-colored facade complemented by a bright red front door. A canopy covers the adjacent carport. The surrounding area includes a grassy yard with scattered trees, creating a serene setting.

Home in Port Republic

5 out of 5 average rating, 43 reviews

Coastal Haven- Beach w/ BBQ

4.95 out of 5 average rating, 20 reviews

Riverview Retreat

A serene sunset is captured over calm waters, with vibrant oranges and yellows reflecting on the surface. The horizon blends into deep blues and subtle cloud formations, while the shoreline features a natural landscape leading to the water's edge.

Home in Tilghman Island

4.93 out of 5 average rating, 29 reviews

Panoramic water views

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 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, 112 reviews

Bungalow Private Beach & Dock Colonial Beach Water

Top guest favorite

The interior space features a well-lit open layout with wooden beams overhead. A dining table sits to the left, while a living area with a comfortable sofa and coffee table is visible. Large windows provide ample natural light, enhancing the inviting atmosphere.

Cottage in Annapolis

4.98 out of 5 average rating, 128 reviews

Weems Creek Cottage, Annapolis Waterfront

The exterior of a quaint cottage is showcased, featuring light-colored siding and a welcoming front door. A small, covered porch is present, providing shelter at the entrance. Lush green grass surrounds the home, complemented by trees in the background and a hint of water visible nearby.

Cottage in California

4.88 out of 5 average rating, 51 reviews

Saint Cozy Cottage | waterfront family getaway

Top guest favorite

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, 103 reviews

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

Top guest favorite

A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.

Cottage in Leonardtown

4.96 out of 5 average rating, 112 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

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, 166 reviews

Waterfront Chesapeake Bay Sunrises & Private PIER!

Cabin rentals with a kayak

The exterior of the historic cabin is showcased, featuring a dark blue facade with a white entrance door. Flowerpots flank the entrance, and landscaped gardens present vibrant floral hues. A glimpse of the dock along the river is visible in the background, framed by mature trees.

Cabin in Queenstown

4.92 out of 5 average rating, 26 reviews

Cozy Historic Cabin on the Water

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.

4.95 out of 5 average rating, 77 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

4.76 out of 5 average rating, 82 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, 32 reviews

Camp Heron : Waterfront Cabin on the Potomac

A serene outdoor space features a fire pit surrounded by white Adirondack chairs. Lush green grass is complemented by vibrant flowers, while trees provide shade. A cabin is visible in the background, showcasing a blend of natural greenery and modern design.

Cabin in Saint Michaels

5 out of 5 average rating, 10 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

A serene coastal scene features a sandy beach lined with gentle waves. Overhanging branches with white flowers frame the view, while a distant pier is visible along the horizon. The sky is bright blue, accented with a few small clouds.

Cabin in Port Republic

4.75 out of 5 average rating, 12 reviews

Ocean Break

An open living area features a comfortable sofa paired with accent pillows, alongside a dining table set with white chairs. The light wooden ceiling is complemented by large windows allowing natural light, while the kitchen area showcases modern appliances and organized cabinetry.

4.86 out of 5 average rating, 44 reviews

Covenant Cove (Cove Point Beach)

A wooden boat dock extends into a calm lake, surrounded by lush greenery. A decorative lighthouse structure stands on the dock, providing a nautical touch. Clear blue skies reflect on the water's surface, enhancing the serene lakefront atmosphere.

4.83 out of 5 average rating, 29 reviews

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

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