Vacation rentals with a kayak in Shenandoah River

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Top-rated kayak rentals in Shenandoah River

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Top guest favorite

The log cabin features a welcoming front porch with seating and vibrant hanging plants. A gravel pathway leads to the cabin, surrounded by green grass and trees, while a fenced area is visible beside the porch, enhancing the private outdoor space.

Cabin in Charles Town

4.97 out of 5 average rating, 237 reviews

Vintage Riverfront Log Cabin “Emma” w/hot tub

“Emma” is a Shenandoah Riverfront Log Cabin hand built in 1900’ , she was just newly renovated. Come, Relax, you are on “River Time”. From the front porch, stroll the yard, and across the road, to access the Shenandoah riverfront dock. Here, the river is wide, and the view is amazing, launch a kayak or tube, fish from the dock. Enjoy your evenings around the campfire. From the cabin, you are just a few minutes away from Historic Harpers Ferry, wineries, breweries, hiking trails Enjoy!

Top guest favorite

A bright living area is presented with large windows allowing natural light to fill the space. Comfortable furnishings include a sectional sofa and a circular coffee table, while a patterned area rug adds warmth. A television is mounted on a dark cabinet, enhancing the room's functionality.

Farm stay in Purcellville

4.98 out of 5 average rating, 143 reviews

50-Acre Farmhouse Getaway Oasis in VA Wine Country

Just 1 hour from Washington DC, the spacious and tranquil Farmhouse at Dogwood Pond resides on 50 acres of land, and includes a large pond equipped for fishing. Our guests enjoy the nearby Purcellville Historic District for quality restaurants and cafes, vintage shopping, and the W&OD trail entrance at the old Purcellville train station. The property is also a swift 20 minute drive to historic downtown Leesburg, Waterford, Harper's Ferry, and endless wineries, breweries, hiking and bike trails.

Top guest favorite

A modern cabin is positioned on stilts, set against a backdrop of lush green trees and the serene Shenandoah River. The exterior features a sleek metal roof and a patio area with chairs, inviting relaxation while taking in the natural surroundings.

Cabin in Woodstock

5 out of 5 average rating, 109 reviews

The Bird's Nest - Cabin by the River

Located on one of the Seven Bends of the Shenandoah River, the Bird’s Nest is a brand new, custom built 800 square foot cabin featuring an open loft with king bed and skylights, steam shower, heated bathroom floor, and gas fireplace. Exterior amenities include a hot tub, gas grill, gas fire pit table, fire pit by the river, and private river access in a peaceful, wooded setting. Kayaks/tubes are available to use to float down the river with the unique ability to park/exit on the hosts’ property.

Superhost

A house with a raised deck and expansive windows overlooks a grassy area. Colorful kayaks are stored on the ground in front of the steps leading to the deck, surrounded by trees that provide natural shade.

Cottage in Shepherdstown

4.91 out of 5 average rating, 286 reviews

Riverfront Cottage in Shepherdstown, WV

Escape to this tranquil, riverfront retreat with stunning, year-round river views, a private dock (available late May-Sept) & firepit. Relax, fish, explore, or visit nearby attractions in Shepherdstown, Sharpsburg, & Harper's Ferry. Two kayaks, a canoe, paddles, & lifejackets are available for your use. All water activities are at your own risk. WV DNR requires all boaters to have a lifejacket and all boats to have a whistle. Please bring your own whistle(s). MD or WV fishing license is fine.

Superhost

A charming cabin is set amidst rolling green lawns, surrounded by mature trees. The picturesque mountains rise in the background under a partly cloudy sky, creating a serene outdoor environment. A gravel driveway leads up to the cabin, welcoming guests to a peaceful retreat.

Home in Rileyville

4.95 out of 5 average rating, 210 reviews

Peaceful River Retreat: Hot Tub, Kayaks & Fire Pit

*Included -4 kayaks & 1 canoe- direct access to private river front use** Perched on 2 acres of riverfront property with over 200 ft of private shoreline on river rapids. Peaceful River has 2 comfortable king, and 2 twin beds and all the furnishings you'll need to enjoy your stay - updated kitchen, spacious screened-in porch, 2 updated full baths, and a separate riverside hot tub area. The wildlife is abundant and the views are peaceful. Enjoy relaxing & exploring as your worries float away.

Guest favorite

A covered outdoor patio is visible, featuring two wicker chairs with cushions and surrounded by planter boxes filled with flowers. A view of well-maintained greenery and a gravel area highlights the peaceful outdoor setting.

Cottage in Marshall

4.89 out of 5 average rating, 110 reviews

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. This property stands out for its limitless outside fun!

Guest favorite

A wooden pier extends into the Shenandoah River, where kayaks and paddleboards are securely stored. Two individuals are seen wading in the water, while another person walks up the steps from the river. Lush greenery surrounds the area, enhancing the natural setting.

Cabin in Luray

4.94 out of 5 average rating, 361 reviews

Riverfront Cabin! Farm, Kayaks, Trail & Fireplaces

Authentic log cabin nestled by the Shenandoah River in Luray, VA. Over 800 5-star reviews! Remote workers paradise! Acres of private riverfront. Use our water equipment and walk the trail. Cozy up next to the wood-burning fireplace in the winter. Easy drive to the Luray Caverns, Shenandoah National Park, George Washington National Forest, Massanutten or Bryce Resorts for skiing, and much more. Fresh farm eggs and firewood sold on site. This year-round cabin is your next vacation!

Superhost

The exterior of the house showcases a modern design with a red facade and multiple levels. Spacious decks are present, providing areas to relax and enjoy nature. Large windows reflect the surrounding greenery, while trees create a tranquil environment.

Cottage in Front Royal

4.94 out of 5 average rating, 101 reviews

Country Elegance overlooking the Shenandoah River

This beautiful home, which we have named The Snug, is a guest favorite in our Rolling River Holidays rental portfolio! The house was designed and built by the owner of the property, Frank O'Reilly, and not a detail was left out. The house is located on a stunning ten acre river site on the 108 acre Rolling River Farm, and is nestled in the trees. Walk out of the back of the house, onto any of the three levels of decks and patios and be met by lovely views of the Shenandoah River.

Guest favorite

An indoor swimming pool is set against a backdrop of large windows, offering views of lush greenery and mountains. Natural light fills the space, highlighting the pool's clear water and smooth tiles. Two ceiling fans provide ventilation above the inviting area.

Cabin in Woodstock

4.9 out of 5 average rating, 113 reviews

Riverfront Luxury Cabin | Pool, Hot Tub & Views

Featured in The Washingtonian as a top DC-area escape! Our Shenandoah Riverfront Luxury Cabin blends romance, family fun, and nature. Minutes from the river with mountain views and close to wineries, breweries, and trails, this 3-bedroom retreat offers a year-round hot tub, a seasonal indoor pool (unheated—fun for summer swims or a refreshing winter dip), king beds, fireplaces, and a starry-sky fire pit. Book your getaway today and ask about seasonal and extended-stay discounts!

Top guest favorite

The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.

Cottage in Green Spring

4.98 out of 5 average rating, 105 reviews

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

Top guest favorite

A serene lake view is framed by bare trees at dusk, with soft colors of sunset reflected on the calm water. The silhouette of a boathouse is visible along the shore, enhancing the tranquil setting.

Chalet in Central City

4.96 out of 5 average rating, 112 reviews

Romantic Lake Front Chalet w/Private Hot tub

A unique and secluded lakefront chalet tucked away in a canopy of beautiful oak trees. Lakefront Libations is located on Indian Lake and boasts modern amenities in the heart of nature. You can relax in the hot tub, kayak on the pristine lake or enjoy your favorite drink by the firepit. This chalet is close to ski resorts, marina, ATV parks, golf courses and the Flight 93 Memorial. Your intimate escape to the Laural Highlands awaits you!

Top guest favorite

A serene view of the Shenandoah River during dawn, featuring still waters reflecting the soft hues of sunrise. The surrounding trees frame the scene, creating a peaceful atmosphere as the early light begins to illuminate the landscape.

Home in Luray

4.99 out of 5 average rating, 170 reviews

Scenic riverfront escape | Cozy family space

Imagine waking up to sunlit mountain views and ending the day riverside with loved ones. Our property offers this serene escape, ensuring relaxation in a scenic setting. One level home with walk out basement. Spacious yet cozy, it comfortably hosts groups up to 10, welcoming pets with open arms. Whether lounging on the deck or exploring the river, find your perfect getaway here. Ready to make memories? Secure your stay today!