Holiday rentals with a kayak in Shenandoah River

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.

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.

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!

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!

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 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.

Romantic Lake Front Chalet w/Private Hot tub

A unique and secluded lakefront chalet tucked away in a canopy of beautiful oak trees. Lakefront Libations is located on Indian Lake and boasts modern amenities in the heart of nature. You can relax in the hot tub, kayak on the pristine lake or enjoy your favorite drink by the firepit. This chalet is close to ski resorts, marina, ATV parks, golf courses and the Flight 93 Memorial. Your intimate escape to the Laural Highlands awaits you!

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!