Vacation rentals with a kayak in Jefferson County

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Top-rated kayak rentals in Jefferson County

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Top guest favorite

A view of the charming two-story home set among tall trees on a well-maintained lawn, showcasing a natural and peaceful setting. The property features a fenced yard and a distant shed, blending well with the surrounding woodland landscape.

Home in Charles Town

4.98 out of 5 average rating, 41 reviews

Shenandoah River House Retreat

New April 2024! We are excited to offer a peaceful wooded retreat for our guests! 4-bedroom (sleeps 8 comfortably) 1.5-bathroom home located on 2.5 acres with the Shenandoah River & Blue Ridge Mountains right outside the front door. Swim, fish, kayak, tube the river, hike the Appalachian Trail, and other trails in the area. Harpers Ferry is 15 minutes away. Unplug, relax, have a bonfire, or watch a movie in front of the cozy warm wood stove. Pets are welcome with a fenced front yard if needed.

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, 238 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

An aerial view showcases the expansive Potomac River surrounded by lush greenery and rolling hills. The property features a large grassy area leading to the river's edge, set against a backdrop of dense trees and distant mountains.

Home in Harpers Ferry

4.96 out of 5 average rating, 144 reviews

Riverfront HarpersFerry! PrivateDock,HotTub,Kayaks

Just 12 min from Harpers Ferry National Historical Park, this recently renovated & refurnished home is located ON THE POTOMAC RIVER! Stairs just off the huge backyard lead you into the river, or take a short car ride to our private riverfront gazebo & fire pit. Hot tub, kayaks, SUP, river tubes & more! Located 1.5 hours from DC and Baltimore, dozens of wineries/breweries within 15 miles, 10 min from River Riders, & 18 min from Charlestown Races & Slots! Golf cart no longer included with rental.

Guest favorite

A grassy pathway leads down to a serene river, flanked by vibrant green trees. Two kayaks are positioned on the bank, ready for use. The calm surface of the water reflects the surrounding foliage, creating a natural and peaceful setting.

Cabin in Harpers Ferry

4.9 out of 5 average rating, 48 reviews

Riverside Retreat on Shenandoah River

Quaint 3 bedroom cabin located on 1.5 acres with direct river access to the Shenandoah River. Great get away from the city! Fishing, tubing, kayaking, swimming, mountain biking, Appalachian/Rolling Ridge Foundation trail hiking, and campfires are within walking distance. Virginia wineries, breweries, white water rafting, casino/horse racing, car racing, Harpers Ferry and Charles Town historic sites are less than 30 mins. from the cabin. Or just listen to nature! Only 90 mins. from DC area.

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, 287 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.

Top guest favorite

Villa in Harpers Ferry

4.99 out of 5 average rating, 81 reviews

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

This the definition of "Wild and Wonderful West Virginia! magical place, a former rock quarry now lagoon. There is no public access to this property. The only access to the Lagoon, Beach and other amenities is via booking or owners explicit permission. This is a complete unit that is on its own level, own access, own parking, own amenities, Owners live on upper level with fully separate entrance, parking, access, etc. No shared internal spaces. Double sound insulation, no noise worries.

Superhost

Two adirondack chairs are positioned on a wooden deck, offering a view of the Potomac River. Kayakers can be seen gliding along the serene water, surrounded by lush green trees that line the riverbank. The scene captures a peaceful moment in nature.

Home in Shepherdstown

4.79 out of 5 average rating, 183 reviews

Plum Lazy on the Potomac

With stunning views and prime river access, Plum Lazy is nestled on three partially-wooded acres sloping gently to the water's edge. Enjoy 150 feet of shoreline with a large landscaped expanse of grass perfect for play, picnics, or just shady naps. This riverfront area is exclusively for you and guests at our cabin on Knott Road. A rocky peninsula extends your riverfront another 100 feet into the Potomac. The large deck and stone patio features a variety of seating options and gas grill.

Guest favorite

The exterior of the Garden Cottage is framed by lush greenery and blooming hydrangeas, creating a serene garden setting. A covered porch features white rocking chairs, inviting relaxation, while steps lead up to the entrance. Sunlight filters through leafy branches, enhancing the tranquil atmosphere.

Guesthouse in Purcellville

4.86 out of 5 average rating, 66 reviews

Garden Cottage

Enjoy this quaint Garden Cottage in the backyard of the 1793 Stone House & experience the tiny town of Hillsboro. Perfect for a couple’s getaway to enjoy Virginia wine country or if you’re coming for a wedding or other event. It’s 5 miles from the Appalachian Trail that’s great for any day-hikers or a nice break for thru-hikers. Like a hotel room, but much better with your own private space & lovely back porch to relax & enjoy the many flowers in the backyard. You won’t want to leave!

Top guest favorite

A charming house is nestled among lush greenery, featuring a warm brick exterior with white trim. The front porch welcomes visitors, framed by well-maintained landscaping and trees, providing a serene outdoor environment.

Home in Harpers Ferry

5 out of 5 average rating, 13 reviews

Wineries-Hot tub-Fire pit-Game Rm-Private-Lg deck

Discover the beauty of Harpers Ferry and the Shenandoah River with this fully equipped house. This spacious retreat offers a hot tub, game room, community river access with two kayaks available for use, and more. Relax in the private hot tub, or enjoy a poker night in the game room, explore nearby hiking and outdoor adventure, visit one of the nearby wineries, explore Harper’s Ferry, or try your luck at Charles Town casino. Relax with the whole family at this peaceful place to stay.

Top guest favorite

A serene view of a dock by the river, featuring kayaks resting on the wooden platform. Lush greenery surrounds the calm water, reflecting the gentle hills in the background. The scene offers a peaceful escape in nature, perfect for leisurely activities.

Home in Charles Town

5 out of 5 average rating, 21 reviews

Stunning View, Riverfront Privacy, 18-Acre Estate!

Escape to our spacious 18-acre estate perfect for large groups to reconnect & unwind. Enjoy privacy, beautiful nature & a range of activities - from relaxing riverside to gathering around the fire pit under the stars. Explore local trails, wineries & breweries. ⭐ “The only downside - that we didn't stay longer!” 🌄 HIGHLIGHTS ✓ Spacious & built for convenience ✓ Beautiful views, riverfront access & proximity to trails ✓ Easy access to wineries, breweries & other local attractions

Guest favorite

A vibrant sunset paints the sky in shades of pink and purple, casting a warm glow over the rolling hills. A grassy foreground leads to trees in the distance, creating a serene natural landscape.

Guest suite in Charles Town

4.89 out of 5 average rating, 45 reviews

Hoping to see a Sasquatch?

Whether you're looking for hiking, river adventures, ziplining, a day at the beach (Mountain Lake Club) or just want to get away for a little R&R our place has it all within 15 to 30 minutes driving. Walking distance to the beautiful Shenandoah river, plenty of space to park if you want to bring a small boat. Spend the day out in nature, then come home to hotel style living. After a nice shower, get the fire pit going and cook out! We love pets!

Superhost

Home in Harpers Ferry

4.83 out of 5 average rating, 29 reviews

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

MOUNTAIN MAMA VACATION HOMES Explore historic Harpers Ferry, charming Shepherdstown, Northern Virginia's wine country, and everything in between while relaxing in our newly renovated, riverfront chalet. This family-friendly home is the perfect quiet escape for you and your children with multiple decks equipped with firepits, opportunities for kayak adventures on the Potomac and cozy hot tub dips and sauna sessions after a day on the water.