Holiday rentals in Woodstock

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.

Rivah Retreat, HotTub~Firepit-Fishing-Deck-Private

Rivah Retreat is a one-of-a-kind luxury getaway tucked away on the pristine North Fork of the Shenandoah River. An expansive retreat and custom cabin spread over six acres of riverfront property located just 90 minutes from the White House. With modern amenities, hot tub, gas fireplace, spacious elevated deck, board games, movies, and so much more! Enjoy fly fishing from the private riverbank, quiet walks, abundant wildlife, smores at the firepit and relaxing. The property is best for adults.

Mountain View Modern Basement Suite*King Bed*Wifi

Amazing Mountain Views from this modern Scandinavian inspired guest suite nestled in the heart of the Shenandoah Valley!! Close to hiking, wineries, the river! Enjoy a cup of coffee on the patio and watch the sun rise over the mountains, unwind and watch a movie on the app connected flatscreen TV, refresh in the oversized shower with multiple heads including a rainfall feature. This two bedroom suite has its own entrance, private covered patio with mountain views and parking spot steps away.

Peaceful Valley Farmhouse; Mountain View, King Bed

Our 1922 Peaceful Valley Farmhouse is in the heart of Woodstock. It is a completely renovated home that provides numerous modern amenities, vintage elegance & charm, indoor/outdoor living and exceptional comfort. Within walking distance to town, you can take advantage of quaint restaurants and shops and lots of history. Nearby is the Shenandoah River, mountain ranges & trails, historic battlefields & museums, award-winning wineries & breweries, antique emporiums and year-round activities!

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

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.

Serendipity Lane Retreat; hot tub, vineyard, river

Welcome to Serendipity Lane Retreat. Perched in the scenic Shenandoah Valley, our cozy retreat boasts unparalleled views of lush grapevines and the rolling peaks of the surrounding mountains. Situated beside the picturesque Shenandoah River and adjacent to the renowned Muse Winery, guests can savor the finest wines mere steps from their doorstep. Whether you're seeking a romantic getaway or an adventurous escape, Serendipity Lane Retreat offers the perfect blend of serenity and excitement.

Little Green Cabin on the River

The Little Green Cabin is a beautifully renovated riverfront retreat nestled along one of the Seven Bends of the Shenandoah River between Strasburg and Woodstock—the perfect escape to relax, unwind, and enjoy the outdoors. INSIDE: Full kitchen, 4 beds, cozy furnishings, electric fireplace, Wi-Fi, and oversized windows and doors with plenty of natural light. OUTSIDE: Large screened-in deck, private river access, 2 fire pits, grill, picnic table, hammock, swing set, and horseshoe pit.

1 Block to Downtown | Historic 3BR Home

Stay in a beautifully restored 19th‑century home in the heart of downtown Woodstock. Just steps from restaurants, shops, and historic sites. This pet‑friendly 3BR, 2.5‑bath retreat sleeps 6 and is thoughtfully equipped with spacious living areas, a fully stocked kitchen, comfortable beds, fluffy towels, and a dedicated office with strong Wi‑Fi for workcations. Ideal for wedding weekends, family visits, or exploring the Shenandoah Valley’s wineries, trails, river, and mountain views.

Fenced yard, fire pit, views, wineries, hiking

Welcome to Ruby's Ranch, our modern farmhouse in the Shenandoah Valley! Amenities: + Fully fenced yard reinforced with chicken wire (nearly half an acre is within the fence) + Wrap-around porch with ample seating + Fire pit + Puzzles, games and books + 10 mins from hiking, wineries, and breweries + Views of two mountain ranges + Patio with outdoor seating for eight and a gas grill + Peloton exercise bike + Pack-n-play and high chair + High speed (300 mbps) cable internet

Cozy Historic Cabin w/ stellar view of Big Schloss

This renovated, 130-year-old cabin is a peaceful retreat surrounded by the George Washington National Forest and five minutes from great hiking at Wolf Gap Recreation Area or Half Moon Trailhead. If hiking isn't your thing, don't worry, the views from the porch are incredible. We suggest grilling out on the wrap-around deck while you watch the deer graze their dinner. Then get a great night's sleep on super-comfortable beds.

Starlight Farmhouse | Dog-Friendly + Mountain View

Starlight Farmhouse is a dog-friendly escape with a large fenced yard, sweeping farm-and-mountain views, and some of the darkest skies in the Shenandoah Valley. One of the valley's original farmhouses, it pairs real history with everyday comfort. Unwind by the fire pit, sway in the hammock, or catch the sunset from the porch — with hiking, ATV trails, and Skyline Drive close by, and Luray Caverns an easy day trip.