Cottage holiday rentals in Woodstock

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Cozy Cottage - HOT TUB | Mountain Views | Pets

Welcome to the Sunrise Cottage! Stay here if you want a secluded retreat in nature, easy access to hiking trails, gorgeous views & charming towns. Listen to the sounds of the farm animals while you relax in the hot tub or on the enclosed porch. Beautifully decorated with a fire pit and grill. Within 30 mins from all the major attractions that the Shenandoah Valley offers like Luray Caverns, Shenandoah National Park, Vineyards. Perfect retreat for some R&R away from the city! BOOKING FOR WINTER!

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Shenandoah Riverfront - Happy Peach Cottage

Come relax at The Happy Peach! Nestled at the base of the Massanutten Mountains on the North Fork of the Shenandoah River (100 feet of frontage), this cozy house is the perfect base for adventures or a restful getaway. Fishing, hiking, rafting, antique shopping, wine tasting, caverns & historic sites are some options. Our 2-bedroom house is an ideal getaway for a small group or family and only a 90-minute drive from DC. And, there's high-speed fiber optic internet for to stay connected.

Shenandoah Riverfront and Mountain View Cottage

The Misty River Cottage is located on one of the seven bends of the Shenandoah River and at the base of the Massanutten Mountain. It was designed, built and furnished with the goal of being one of the nicest options in the Shenandoah Valley. With views of the river and mountains from every room. Ensuite bathrooms in each of the two bedrooms. A custom built bunk bed for larger groups. Heated floors, spectacular outdoor space and direct river access all within a short drive to Woodstock.

The Cottage

Need some time to refresh? Spending time in the foothills of the Skyline Drive at our cozy cottage may be for you. Well behaved dogs are welcome but not on furniture. The driveway is long and home is very secluded. Winter access will be subject to weather conditions. Driveway does not get plowed and gets rutty during rainy periods. Cell service is spotty on Browntown road. The cottage has a landline and wifi. Use your wifi calling feature for cell phone use. More info under photos.

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.

Fall foliage soon! Coffee bar, swim, fish, firepit

PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

Hot Tub~WiFi~Views

Escape to a charming one-bedroom Blue Horizon Cottage nestled in the serene mountains, offering breathtaking views of the Blue Ridge Mountain. Relax in the oversized hot tub on the spacious deck, surrounded by National Forrest and nature's beauty. This cozy retreat provides the perfect blend of comfort and tranquility. With easy vehicle accessibility, you can easily reach this idyllic getaway for a peaceful and rejuvenating experience.