Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

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Top guest favorite
The cabin is nestled among tall trees, supported by stilts. Its architecture features a combination of dark siding and wooden beams, with a spacious deck visible, furnished with outdoor seating. Natural greenery surrounds the structure, creating a peaceful atmosphere.
Cabin in Woodstock
5 out of 5 average rating, 135 reviews

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.

Top guest favorite
Two black Adirondack chairs are positioned on a grassy area next to the river, offering serene views of the water and surrounding trees. Gentle sunlight filters through the leaves, creating a peaceful atmosphere for relaxation.
Cabin in Woodstock
4.96 out of 5 average rating, 136 reviews

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.

Top guest favorite
The covered patio features two comfortable sofas and a dining table, all arranged around a central gas fire table. The surrounding landscape offers expansive views of the mountains, complemented by a soft sunset sky.
Guest suite in Woodstock
4.95 out of 5 average rating, 492 reviews

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.

Top guest favorite
A spacious backyard is captured at dusk, featuring a wooden deck with comfortable seating underneath warm string lights. The fully fenced yard showcases a well-maintained lawn, and the renovated farmhouse glows in the background, highlighting its inviting atmosphere.
Home in Woodstock
4.98 out of 5 average rating, 126 reviews

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!

Top guest favorite
Home in Edinburg
4.99 out of 5 average rating, 443 reviews

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.

Top guest favorite
A welcoming single-story house is shown, featuring a front yard with neatly arranged shrubs and flowers. A pathway leads to the entrance, which is flanked by potted plants. A carport is visible on one side, providing covered parking.
Home in Edinburg
4.98 out of 5 average rating, 646 reviews

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

Top guest favorite
A spacious outdoor patio area is visible, featuring seating arranged for relaxation. Trees line the bank of the river, with open fields on the opposite side. The clear water reflects sunlight, and the mountains are visible in the background under a bright blue sky.
Cottage in Woodstock
4.99 out of 5 average rating, 114 reviews

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.

Top guest favorite
A cozy living area features a day bed adorned with decorative pillows, complemented by a large area rug. A small dining table for two is positioned nearby, with a light source illuminating the space. Decorative wall art and a window dressed with curtains add to the charm.
Guesthouse in Woodstock
4.97 out of 5 average rating, 167 reviews

Cozy cottage nestled on 8 acres with mountain view

Relax and enjoy this cozy, yet luxurious space! Enjoy Mountain Views at sunrise and sunset. Besides the resident horses, you will enjoy seeing deer, rabbits, raccoons and many others. We are located a very short drive from Seven Bends State Park, the Shenandoah River and Muse Winery….as a matter of fact, you could walk! Located within minutes of everything, we are also close to Civil War museums/Historic sites, natural caverns and caves, etc. I may even bake for you, if you’re lucky!!

Top guest favorite
Home in Woodstock
4.98 out of 5 average rating, 135 reviews

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.

Guest favorite
An outdoor seating area is showcased, featuring two rod iron chairs positioned around a small round table. The scene is framed by vibrant autumn leaves, with a carpet of fallen leaves on the ground, creating a serene garden setting.
Guest suite in Woodstock
4.87 out of 5 average rating, 344 reviews

Easy, Private and Peaceful, 2 minutes from I-81

Relax in a quiet private suite right off I-81. It's clean and sanitized following CDC guidelines. A self check-in touch pad lock for ease of entry and exit. Located 2 minutes from historic Woodstock, minutes from wineries, breweries, the Shenandoah River, State and National Forests. Private entrance, yard and parking. Comfortable and cozy queen sized bed, kitchenette, coffee maker, microwave, refrigerator, bathroom and shower with WiFi

Guest favorite
A cozy living room features a comfortable green sofa complemented by red chairs. Soft lighting is provided by table lamps on either side. Two windows allow natural light to fill the space, while decorative artwork and a clock enhance the inviting atmosphere.
Home in Edinburg
4.95 out of 5 average rating, 170 reviews

The Cozy Cottage-2 mins to I-81

Kick back and relax in this calm, stylish cottage. Welcome to "The Cozy Cottage". Escape the mundane and embark on outdoor adventures like fishing, hiking, rock climbing, zip-lining, history, wineries, breweries, antiquing and more from this vacation Cozy Cottage just 2 miles from I-81. We are located in Edinburg, Virginia. This 2-bedroom, 1-bathroom house offers all the modern amenities of home in a cottage-inspired living space.

Top guest favorite
A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.
Cabin in Fort Valley
4.98 out of 5 average rating, 123 reviews

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!

Popular amenities for Woodstock vacation rentals

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$29,239 GYDG$30,701 GYDG$27,151 GYDG$29,657 GYDG$29,657 GYDG$29,657 GYDG$29,448 GYDG$33,625 GYDG$28,195 GYDG$34,251 GYDG$29,448 GYDG$28,821 GYD
Avg. temp-3°C-2°C2°C8°C13°C16°C18°C18°C15°C9°C4°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Woodstock?

    Staying near the historic downtown places guests within walking distance of shops, galleries, and restaurants. For a quieter experience, cabins or homes around the edges of town provide a peaceful retreat among trees and farmland.

  • What are the best things to do in Woodstock with kids?

    Families often explore playgrounds, visit locally rooted museums, or enjoy nature trails and easy outdoor adventures around Woodstock. The area has picnic spots, seasonal festivals, and hands-on learning opportunities for kids.

  • What are some of the best things to do in Woodstock?

    Walk through the historic downtown, hike up to Woodstock Tower, or browse markets and galleries featuring regional art and produce. Guided tours, seasonal festivals, and river activities are often suggested for a full experience.

  • How is the weather in Woodstock?

    Woodstock experiences four distinct seasons, with winters around 18–38°F (-8–3°C) and mild summers near 56–74°F (14–23°C). Rainfall is spread throughout the year, so packing layers and a light rain jacket is helpful.

  • When is the best time to visit Woodstock?

    Late spring and early fall are frequently suggested for visiting Woodstock due to mild temperatures and changing foliage. Many enjoy local festivals and outdoor activities during these seasons.

  • What are the best places to visit in Woodstock?

    Many explore downtown Woodstock’s historic district, local museums, and scenic green spaces around the town. The Woodstock Tower provides broad valley views, and visiting nearby farms connects guests with the area’s agricultural heritage.

  • What are some hiking trails in Woodstock?

    Explore nature paths winding through wooded areas and scenic overlooks near Woodstock, including trails in local parks and along the riverfront. Hikers frequently enjoy a mix of easy walks and hilly terrain.

  • What are some family activities we can do in Woodstock?

    Woodstock has parks with playgrounds, walking paths, and picnic areas, making outdoor play appealing for families. Exploring the historic downtown and attending local fairs or markets are frequently suggested group activities.

  • What are some of the best day trip ideas from Woodstock?

    Consider exploring natural parks in the Shenandoah Valley, historic caverns, or nearby vineyards for tastings. Outdoor activities such as canoeing, cycling, and birdwatching are frequently enjoyed just outside Woodstock.

  • Are there any pet friendly accommodations available in Woodstock?

    Many vacation rentals in Woodstock welcome pets, including options with yards or proximity to parks and trails. It is a good idea to check listing details or reach out in advance to confirm pet amenities.

  • What are some local tips for visiting Woodstock?

    Locals suggest starting mornings at a bakery or café and exploring downtown’s shops. Early arrivals at markets yield the best produce, and many recommend catching a sunset from one of the nearby overlooks.

  • What is Woodstock known for?

    Woodstock is known for its historic downtown, local festivals, and scenic views of the Shenandoah Valley. The area’s agricultural roots, mountain landscapes, and small-town traditions all contribute to its distinct character.

  • What are the best hidden gems to explore in Woodstock?

    Woodstock has quiet nature trails, locally owned shops, and art galleries that showcase regional creativity. Exploring walking paths near the river or discovering historic buildings provides a glimpse into the area’s character.

  • What are the best foods to try in Woodstock?

    Woodstock has locally-inspired dishes such as apple-based desserts, traditional American comfort foods, and specialties made from Shenandoah Valley produce. Regional markets and family diners highlight seasonal ingredients.

  • What should I bring for a trip to Woodstock?

    Pack comfortable walking shoes, layers for changing mountain weather, and a rain jacket for occasional showers. A hat and sunscreen are useful for summer, while a warm coat and boots are often needed in winter.

  • What is the nightlife in Woodstock like?

    Woodstock has a relaxed nightlife scene with casual pubs, local breweries, and spots featuring live music on some evenings. Community events and gatherings frequently highlight the area’s friendly spirit.

  • What are the most popular events or festivals in Woodstock?

    Woodstock celebrates with events like classic car shows, agricultural fairs, and seasonal markets, often on holiday weekends or during fall harvest. Music gatherings and craft festivals are also commonly enjoyed by visitors and residents.

  • Are there family friendly vacation rentals in Woodstock?

    Woodstock has many vacation rentals that welcome families, including homes, cabins, and apartments with multiple bedrooms and kitchens. Many listings are designed to accommodate a comfortable stay for groups of all ages.

Quick stats about vacation rentals in Woodstock

  • Total vacation rentals

    Explore 20 vacation rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at G$12,531 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Woodstock vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Virginia
  4. Shenandoah County
  5. Woodstock