Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Woodstock
5 out of 5 average rating, 142 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.

Guest favorite
Cabin in Maurertown
4.95 out of 5 average rating, 113 reviews

MountainWaters-Mtn, River, Relax

MountainWaters is a quiet mountain & river front retreat. Wake up & enjoy a coffee while gazing at the stunning mountain, admire the sun glistening on top the Shenandoah River, listen to birds singing. Take a 3-5min. stroll to your private acre of riverfront. Enjoy use of fire pit, kayaks, fishing poles & Adirondack chairs. Grill up dinner & end the night with a dip in the hot tub watching nature's fireworks (fireflies). Hike and explore cool towns Woodstock and Strasburg. Adventure Awaits!

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, 509 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 cozy sleeping area is featured, with a spacious bed adorned with neutral bedding and decorative pillows. Natural light fills the room through large windows, highlighting wooden shelves lined with plants and decorative items. A comfortable armchair adds to the warm ambiance.
Tiny home in Woodstock
4.98 out of 5 average rating, 109 reviews

Go Tiny on the Shenandoah River

Welcome to the Little Patriot! This brand new tiny house sits on a 100-acre private farm surrounded by a full mile of Shenandoah River frontage with sweeping views of the Blue Ridge Mountains. Enjoy complete privacy as you watch deer stroll by and eagles soar overhead, then take a short stroll to fish or skip rocks in the river. Fall asleep looking up to a big sky of stars then wake up to a coffee on the back porch. Just minutes from Historic Woodstock with quaint shops and cute restaurants.

Top guest favorite
A charming country home is set amid colorful autumn foliage. The residence features a welcoming porch and a well-maintained yard, with a natural stone wall bordering the property. Towering trees surround the house, enhancing the serene countryside atmosphere.
Home in Edinburg
4.99 out of 5 average rating, 453 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 serene riverside view is showcased with green trees framing a calm water surface. A red umbrella provides shade over a seating area with black chairs, while American flags stand near the floating dock. The gentle landscape includes a gravel path leading to the water's edge.
Cottage in Woodstock
4.99 out of 5 average rating, 121 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
Guesthouse in Woodstock
4.97 out of 5 average rating, 174 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
Guest suite in Edinburg
4.99 out of 5 average rating, 473 reviews

Private Apartment, King Bed, Easy access to I-81

Our home is located in the heart of the beautiful Shenandoah Valley . Close to historic towns, Civil War battlefields, wineries, breweries, distilleries & hiking trails. Access to Shenandoah National Park/Skyline Drive's Thornton Gap entry is 40 miles from Edinburg. Shenandoah Caverns is minutes away & Luray Caverns is 35 minutes away. Less than 35 minutes from JMU & EMU. Easy 2 minutes access to Interstate I-81. Pets: Case-by-Case. Due to allergies "No Cats". See instructions below.

Top guest favorite
Home in Woodstock
4.98 out of 5 average rating, 136 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.

Top guest favorite
A private patio features two wooden reclining chairs positioned on a patterned rug. A wood-burning hot tub is nestled to one side, surrounded by lush greenery. String lights hang overhead, providing a subtle illumination against the backdrop of a clear blue sky.
Cabin in Star Tannery
4.96 out of 5 average rating, 279 reviews

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

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
4.88 out of 5 average rating, 352 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
Cabin in Wardensville
4.94 out of 5 average rating, 188 reviews

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.

Popular amenities for Woodstock vacation rentals

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 474ﺩ.ﺇ 474ﺩ.ﺇ 496ﺩ.ﺇ 521ﺩ.ﺇ 521ﺩ.ﺇ 521ﺩ.ﺇ 518ﺩ.ﺇ 591ﺩ.ﺇ 496ﺩ.ﺇ 602ﺩ.ﺇ 518ﺩ.ﺇ 507
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 ﺩ.ﺇ 220 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