Vacation rentals with a kayak in Loudoun County

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Top-rated kayak rentals in Loudoun 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

4.97 out of 5 average rating, 37 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, 232 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, 142 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.

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

4.88 out of 5 average rating, 42 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

The exterior of the historic stone home features a vibrant red front door framed by lush greenery. Flower pots with red blooms are positioned on either side, adding a touch of color. Stone steps lead up to the entrance, surrounded by well-maintained landscaping.

Home in Purcellville

5 out of 5 average rating, 31 reviews

Historic 1793 Stone House

Feel at home in this unique property in western Loudoun County, where it’s easy to visit numerous wineries, breweries & distilleries. Located in the historic town of Hillsboro is this stone home built in 1793 & restored in 2014 w/ exposed interior stone walls & original log beam ceilings w/ a fireplace in each room; a cozy country kitchen & bathroom downstairs, plus a modern bathroom & laundry/dressing room upstairs. The backyard always has something interesting to enjoy no matter the season.

Superhost

A Cape Cod style home is shown, featuring a brick and siding exterior. Green grass surrounds the property, and flowering shrubbery blooms near the entrance. Steps lead up to the front door, framed by large windows that enhance the light-filled atmosphere.

Home in Harpers Ferry

4.82 out of 5 average rating, 230 reviews

Large Home, Hot Tub, Large Wooded Rear Yard/Annex

Country Roads Inn- Huge Cape Cod style home in a partially wooded setting adjacent to River Riders Adventure Resort with evening sunset views, a hot tub, huge yard and lots of space for your group. Twin kitchens, cookware, dining space for 20 and a full finished basement mean plenty of place for your group to gather. Starting 4/13/25 Additionally when PAYING FOR EXTRA GUESTS, we have an annex with 3 extra bedrooms, a kitchenette, and 2 full baths. Must pay for 16 guests to access to all rooms.

Guest favorite

A bay window with diamond-shaped panes allows natural light to fill the space. Soft, checked curtains frame the window, providing a view of the surrounding greenery and seasonal colors outside. A tiled floor complements the neutral tones of the walls and cabinetry.

Farm stay in Catharpin

4.93 out of 5 average rating, 54 reviews

English Tudor Cottage

Take it easy at this unique and tranquil getaway. The guest cottage at Heritage Springs is on a working micro-farm with lovely views of gardens, a pond, and spacious woods. The cottage is situated far enough out of the way that you would never know you were on a micro-farm unless you decide to walk over to the barn. The cottage is 45 min. from Washington DC, but is surrounded by nature. Explore the woods, stroll the path around the pond, or take a walk to visit the animals- relax & enjoy!

Guest favorite

An aerial view captures the expansive 10-acre property alongside the Potomac River, surrounded by lush greenery and rolling hills. The home is positioned centrally within the landscape, with the river glistening in the distance and wooded areas enhancing the natural setting.

Home in Leesburg

4.97 out of 5 average rating, 122 reviews

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

Welcome to Potomac Overlook Farms, where comfort meets nature on 10 acres along the Potomac River. Surrounded by wineries, breweries, and historic towns, this 5,000 square foot estate offers access to adventure and relaxation. The spacious home comfortably sleeps 16, with an optional guest house for 5. Please inquire about the guest house at booking. Our property, unfortunately, does not offer wheelchair accessibility. The pool is available for your enjoyment from April 1 to October 1.

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

4.91 out of 5 average rating, 104 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!

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, 18 reviews

Riverfront Retreat! Relaxing 5-BR w/ Scenic Views

Escape to a private Shenandoah River retreat with 800 ft of riverfront, kayak access, and a twinkle-lit fire pit! ⭐ “The only downside - that we didn't stay longer!” - 5BR, 4BA home sleeps 13 and features a chef’s kitchen, multiple lounges with Smart TVs, board games, Wi-Fi, and a workspace. - Relax on the screened porch or explore nearby trails, wineries, and breweries. - Includes washer/dryer, A/C, central heat, grill, and free parking, perfect for family trips or group getaways.

Superhost

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, 4 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.

A spacious living area features a comfortable seating arrangement and a coffee table on a decorative rug. Large glass doors offer views of the outdoor deck and rolling hills beyond, enhancing the connection to nature. A ceiling fan and wood beams add to the inviting atmosphere.

Home in Charles Town

4.84 out of 5 average rating, 58 reviews

Modern Country House on the Shenandoah River

Come and immerse yourself in year-round nature and the beauty of the Shenandoah River and Blue Ridge Mountains, 70 mins from DC! There are 3 bedrooms and 3 full baths, and plenty of indoor and outdoor space to relax in. Swim, float or kayak on the Shenandoah river, hike the Appalachian trail and visit many award winning wineries & breweries, farms, charming historical towns. Adventure, history, nature, winery and breweries, relaxation, there’s something for everyone!