Cottage holiday rentals in Warren County

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!

Shenandoah River View Retreat *Riverfront*

Take a break from city life and unwind at our peaceful Shenandoah Riverview Retreat. On our property you can fish, swim, kayak, and float on the south fork of the Shenandoah River. If the river is not your thing then hike, bird watch, visit wineries, tour caverns, and so much more! Take in the golden hour as it dips over the Massanutten Mountain and the George Washington National Forest. This cottage has been an escape for our friends and family for years, and now it is available to you.

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.

Bluebird Cottage at Shenandoah

Nestled in the hills of the Blue Ridge Mountains you will be delighted at this unique and tranquil getaway. Enjoy scenic views while sipping a glass of wine from any of the short distance local wineries, a hot cup of coffee, or your favorite spirit from the comfort of your own front porch or back deck. The Bluebird Cottage is your destination to reconnect with nature and ease your busy lifestyle. Hike the nearby Appalachian trails, visit local caverns, or go tubing in the Shenandoah River.

Shenandoah Escape, Hot Tub, Kid-Friendly, Hiking

Step into our tranquil retreat, a charming cottage overlooking breathtaking Shenandoah. From the wrap-around porch, soak in sweeping vistas of lush greenery and the Shenandoah river creating an idyllic backdrop for relaxation. Inside, find comfort in cozy furnishings and thoughtful touches, inviting you to unwind and recharge. Whether you're savoring a morning cup of coffee or embarking on an adventure along nearby hiking trails, this peaceful haven offers an escape into nature's embrace.

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.

New! Family cottage w/ fast WiFi & pet friendly.

We are centrally located near some of the best attractions in VA. The Famous Apple House is only 5 mins away. The home features a gourmet kitchen - fully stocked. Gig WiFi, 3 nicely sized bedrooms. Traverse downstairs we have big screen tv, board games, ping pong, or play on the popular arcade machines. Have a glass of wine on the deck or make s’mores near the fire pit. There is a little bit for everyone here. We would love to host you for your next getaway. Message me anytime!

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.

Riverfront: HotTub, Sauna, ColdPlunge, FirePit

Welcome to Ultimate River Paradise, a secluded retreat with 300 ft of private Shenandoah River frontage! Relax in the hot tub, unwind in the wood-burning Cedar Sauna with Cold Plunge and the Riverview, or gather by the firepit under the stars. Enjoy a movie room, shuffleboard, ping-pong, trampoline, and outdoor deck with stunning views. Sleep in luxury with three king beds and enjoy a fully equipped kitchen. Escape, unwind, and create unforgettable memories—book your stay today!

The VUE - On Top of Paradise - all inclusive!

Situated on a mountainside, the Vue blends luxury with nature. The spacious deck offers stunning mountain views, while the open-concept kitchen and living area with a grand fireplace make it feel like home. Hot tub with mountain views! With no steps at the entrance, it's designed for easy access. You'll reach The Vue via a well-maintained gravel road. 4WD or AWD is recommended from November to April, though 2WD is usually fine the rest of the year. Parking Max 4 vehicles

Willow Wind Cottage

Cozy cottage , writers retreat Whether you want a Romantic getaway, planning a girls' trip, or just looking for a quiet Writers retreat. The cottage is nestled in the woods just minutes from the many attractions that bring visitors to the Shenandoah Valley And Front Royal VA. Immerse yourself in nature. Just minutes from the Shenandoah River, Skyline Drive, Caverns, Many Wineries, Breweries Restaurants, numerous outdoor attractions Hiking trails, and Canoe trips.

The Apple Mountain House

Perched on a mountainside, this 4BR, 3BA retreat offers breathtaking views of rolling farmland and a river. Relax on the spacious deck, soak in the hot tub, or enjoy the rec room with a poker table and dart board. The open living space features floor-to-ceiling windows, a cozy fireplace, and a modern kitchen. With high-speed WiFi, Smart TVs, and a fire pit, it's the perfect getaway. Wake up to the view of a lifetime! AWD is recommended Nov-April