Holiday rentals with a kayak in Shenandoah River

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!

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.

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.

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!

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.

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.

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Riverfront Cabin! Fireplaces, Farm, Kayaks & Trail

Authentic log cabin nestled by the Shenandoah River in Luray, VA on our hobby farm. 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.

Beautiful Log Cabin in Private WV Mountains

We love our private log cabin set far back from the gravel road, deep in the West Virginia mountains. 20 min from Berkley Springs, 3 min drive to the river w/ private access & 2 hours from DC / Baltimore. - The log cabin style is spectacular - Gigabit Fiber Wifi & ethernet - Sit/Stand desk w/ 27" 4k monitor - 42" TV w/ roku ultra & blu-ray - Game table w/ board games - Infant & Toddler friendly - Super dog friendly - Fire pit, grill & fireplace

Riverfront cabin with new hot tub

Welcome to our waterfront cabin on the Shenandoah River with all the comforts of home right at the water's edge. * 2 Queen BR's, 1 bath. * Fully equipped kitchen * Gas fireplace * Screened-in porch w/riverfront views, gas grill + private hot tub * Outdoor fire pit + picnic area w/private river access * Kayaks, canoe & tubes to use during your stay. * Dogs are allowed for an additional fee (See details of price breakdown in our listing.)

Cottage Escape in Virginia Wine Country

Tucked among rolling hills, this cozy cottage rests on 25 acres with a private lake just beyond your door. Sip wine beneath the stars, paddle at sunrise, or wander where the wildflowers grow. Just minutes from vineyards, brews, and historic charm, it's a perfect escape to slow down and reconnect. You may hear the laughter of our little ones nearby—just part of the magic here at the farm. We can't wait to welcome you.

River & Mtns | Hot Tub, Kayaks & Fire Pit

Relax and explore at Peaceful River Retreat, a private 2-acre Shenandoah River retreat with 200+ ft of shoreline. Enjoy direct river access, a riverside hot tub, 4 kayaks & a canoe, 2 king beds, 2 double beds, sectional couch, a screened-in porch with water views, and plenty of games/activities provided. Perfect for relaxing, adventure, wildlife, and making unforgettable memories! 🌿✨