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 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.

Top guest favorite

A wooden deck offers a serene view of the surrounding mountains and the river below. Two striped chairs are positioned alongside a circular table, inviting relaxation while enjoying the natural scenery. Bare trees enhance the tranquil atmosphere of this outdoor space.

Cabin in Maurertown

4.95 out of 5 average rating, 100 reviews

MountainWaters-Mtn, River, Relax

MountainWaters is a quiet mountain & river front retreat. Wake up & enjoy a coffee while gazing at the stunning mountain, admire the sun glistening on top the Shenandoah River, listen to birds singing. Take a 3-5min. stroll to your private acre of riverfront. Enjoy use of fire pit, kayaks, fishing poles & Adirondack chairs. Grill up dinner & end the night with a dip in the hot tub watching nature's fireworks (fireflies). Hike and explore cool towns Woodstock and Strasburg. Adventure Awaits!

Guest favorite

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 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. Please be mindful this property is near a train track, charming!

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.

Top guest favorite

A peaceful vacation cottage is surrounded by vibrant fall foliage, reflecting beautifully in the tranquil pond. The property features a grassy area with outdoor seating, inviting guests to relax and enjoy the serene natural surroundings.

Home in Clearville

4.93 out of 5 average rating, 307 reviews

Grouseland's Pondside Vacation Cottage

Set about a quarter mile of the road, our pet friendly solar powered vacation cottage is a perfect getaway for anyone trying to spend some alone time with nature! Guests have complete privacy inside the cottage with a full kitchen, two TV's, Wi-Fi, and a mini split system for heating and cooling. As well as exclusive access to the hot tub, fire pit and pond outside! We also have various shared hiking trails through the woods surrounding the cottage for campers and cottage guests to enjoy!

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.

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 spacious bedroom features exposed wooden beams and rustic log walls. A plush white bed is centered in the room, flanked by two bedside tables with lamps. A wooden wardrobe and an armchair are positioned by the window, enhancing the cozy atmosphere.

Guesthouse in Waterford

4.92 out of 5 average rating, 125 reviews

Cabin On The Creekside

Cabin on the Creekside is a log cabin located on beautiful wooded property just outside of Waterford, VA. The cabin is a perfect spot to unwind, relax, and come explore Loudoun County which is filled with wineries, breweries, farm to table restaurants, hiking trails and more! Beautifully decorated space, king size bed, large comfy couch, 75 inch TV, and kitchenette are a few highlights of the space. Looking forward to your stay!

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!