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, 126 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
The charming cottage is nestled on a grassy area, framed by trees. A welcoming front porch and steps lead to the entrance. Two outdoor firepits can be seen nearby, providing cozy spots for gatherings under the evening sky.
Cottage in Mount Jackson
4.93 out of 5 average rating, 109 reviews

Hot Tub!, 2 Fire Pits, Huge Deck, Private orchard!

The home is an adorable cottage perfect for both a romantic getaway or a family/friends retreat. Enjoy views of the small orchard on the 3 acre wooded property from the large deck and two firepits. The Orchard Cottage is a great base to explore local wineries, hiking, and nearby Bryce Resort. Conveniently located 2 hrs from DC, 45 minutes from Harrisonburg, and only 12 minutes from Bayse/Bryce Ski Resort. Only a 15 min drive to I-81 to conveniently access all the Shenandoah Valley has to offer

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, 475 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 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, 433 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
4.97 out of 5 average rating, 618 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 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, 163 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
Two dogs are seated on black chairs in a grassy area, facing a charming cottage with a stone chimney. The house, featuring numerous windows, is surrounded by a spacious wooden deck. A fire pit is visible in the foreground, providing a cozy gathering spot.
Cottage in Fort Valley
4.96 out of 5 average rating, 237 reviews

Cozy Cottage/Pet Heaven

Deep breath...exhale. Looking for the perfect place to hideaway? You have found it. Enjoy big skies, picturesque landscapes, friendly farm animals and colorful sunsets. Nestled in the valley within the valley, you are surrounded by the George Washington National Forest. Offering hiking, biking, ATV trails, and so much more. Skyline Drive and Luray Caverns are just a 30 min drive. 30 minutes to shopping. Located less than 2 hours west of DC. Come see what you have been missing.

Guest favorite
A welcoming porch features two white rocking chairs positioned around a small table. A decorative wreath adorns the window, while subtle outdoor lighting adds warmth. A striped rug lies beneath, and potted plants can be seen providing a touch of greenery.
Home in Edinburg
4.92 out of 5 average rating, 225 reviews

Charming, Parkview Cottage, King bed, 1 mi to I-81

Welcome to Parkview Cottage you will love this Cozy, 1940's home for a quiet fun getaway or quick overnight stay located in small rural town with an easy 1 mile from I-81. Enjoy quiet mornings on the porch watching the sunrise and a few neighbors stroll by out on morning walks and then venture off for the neighboring park, a hike, canoe trip, trip to the caverns or wineries close by. Enjoy the sunset from the sunroom over Edinburg Park. Park under the oversized "2 car" carport.

Top guest favorite
The exterior view of the cottage features a walkway leading to a white door, flanked by climbing roses and hanging flower pots. A small outdoor table and chairs are set on the gravel, inviting guests to enjoy the pleasant surroundings.
Guesthouse in New Market
4.98 out of 5 average rating, 450 reviews

Stay in a piece of history! Private Entire Cottage

Built in 1797, this cottage sits next to the historic William Rupp House, and is #17 on the self-guided walking tour! Although you are staying in a piece of history, you still get the privacy you need to comfortably explore all Shenandoah Valley has to offer. 19.6 miles away from JMU, 5.2 miles away from Endless Caverns, right off Interstate 81, and within walking distance of local stores, coffee shops, and restaurants... buckle in for a load of fun with this convenient location.

Top guest favorite
An aerial view captures the charming residential area, showcasing a row of 19th-century homes with distinctive metal roofs. The foreground displays a tree-lined street, leading to nearby historic sites, restaurants, and shops, all within a block's distance.
Home in Woodstock
4.98 out of 5 average rating, 132 reviews

Historic Charm meets Modern Luxury @OnCloudWineVA

Experience the charm of Woodstock, VA at On Cloud Wine a spacious, pet-friendly 19th-century gem just steps from history, restaurants, shops, cafes, and a movie theater. This 3 bedroom, 2.5 bath home features generous living space, a stylish bar room, full kitchen, and a remote work-ready office perfect for longer stays. Minutes from wineries, hiking, fishing, and Shenandoah River adventures. Comfort, character, and convenience all in one unforgettable getaway.

Guest favorite
A spacious deck features multiple Adirondack chairs arranged for enjoying scenic mountain views. The area is illuminated by natural light, with a wooden railing framing the outdoor space. The surrounding trees add a touch of greenery to the serene environment.
Cabin in Lost River
4.95 out of 5 average rating, 206 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

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, 338 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

Popular amenities for Woodstock vacation rentals

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$29,268 GYDG$30,732 GYDG$27,178 GYDG$29,686 GYDG$29,686 GYDG$29,686 GYDG$29,477 GYDG$33,658 GYDG$28,223 GYDG$34,286 GYDG$29,477 GYDG$28,850 GYD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Woodstock?

    Four-legged friends are welcome in Woodstock. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Woodstock?

    Yes! Work meets play with ease at over 10 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Woodstock?

    Experience the best of Woodstock with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Woodstock have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Woodstock?

    Woodstock has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Woodstock have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Woodstock. Enjoy a tailored experience with all the comforts you desire.

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$12,544 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,510 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

  • 5 Average rating

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

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