Holiday rentals with a kayak in Shenandoah River

Pio- New cabin! Riverfront!

*Built in 2024 * No pets *On the Shenandoah River *River frontage *Stairs into water *Beautifully crafted cabin *4 beds *Electric fireplace *42” smart tv lvgrm, 32”smart tv Br1 *Starlink wifi *Use your streaming service *Cozy and inviting *Deck area with stools and other seating *Fire pit, surrounded by Adirondack chairs *Gas grill *35 min Shen. N. P/ Skyline Dr. *26 minutes to Kennedy Peak Trailhead *5 min to boat launch *29 minutes to groceries *Shop first *26 min to Luray Caverns

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.

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!

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!

Farm Stay in a luxury tiny home with hot tub

Welcome to “Horsefeathers” a tiny home on an historic property where you will be immersed in a farm experience! Although tiny, this house is equipped with all top of the line luxuries to include a personal hot tub, an automatic cappuccino maker, a king nectar mattress-just to name a few. Only minutes to Winchester the location is convenient to restaurants and shopping yet you’ll feel like you have been transported back in time to a working homestead where you can interact with all the animals.

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.

Fall Riverfront Getaway with Hot Tub & Kayaks

Your own private slice of the Shenandoah River. Wake up to river views, spend the morning kayaking from your private waterfront, gather around the fire pit in the afternoon, and end the day soaking in the riverside hot tub under the stars. Perfect for couples, families & friends looking to recharge in nature while enjoying cozy comforts and memorable outdoor experiences. A short drive to Luray Caverns, Shenandoah National Park, beautiful Skyline Drive, hiking + biking trails, wineries + more!

Riverfront Cabin! Farm, Kayaks & Fireplace (DB)

Historic modernized riverfront log cabin with hand hewn logs nestled by the Shenandoah River in Luray, Virginia on our farm. Over 800 5-star reviews! Remote workers' paradise! Acres of private riverfront with water equipment and trail. Cozy up next to the wood-burning fireplace or enjoy your own campfire! Easy drive to the Luray Caverns, Shenandoah National Park, George Washington Forest, Massanutten or Bryce Resorts for skiing, and much more. Fresh farm eggs and firewood sold on site.

Spend a spectacular September at The Snug!

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 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.

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.)