Holiday houses in Woodstock

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Top-rated holiday rentals in Woodstock

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Top Guest favourite
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, 130 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 favourite
Cabin in Woodstock
4.87 out of 5 average rating, 134 reviews

Shenandoah Riverfront w/ Hot Tub & Cold Plunge!

Escape to Agua Serena, a peaceful Shenandoah Riverfront retreat where families, couples & small groups unwind w/ mountain views & cozy nights by the fire. Enjoy the hot tub, seasonal indoor pool, nearby hikes, wineries & stargazing. ⭐ “Beautiful, peaceful, and relaxing—the perfect getaway!” – Miriam 🌄 HIGHLIGHTS ✓ Riverfront views & access, hot tub & seasonal indoor pool (cold plunge in the Winter!) ✓ Family-friendly w/ toys, games ✓ Near wineries, Shenandoah hikes & small towns

Top Guest favourite
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, 478 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 favourite
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, 436 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 favourite
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, 628 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 favourite
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, 110 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 favourite
Home in Woodstock
4.98 out of 5 average rating, 134 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 favourite
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
4.93 out of 5 average rating, 228 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.

Guest favourite
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, 340 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 favourite
A seating area is arranged on a wooden deck, facing a stunning view of the valley. Comfortable chairs and a couch are positioned to enjoy the colorful sky at sunset, creating a serene atmosphere for outdoor relaxation.
Cabin in Wardensville
4.95 out of 5 average rating, 180 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.

Top Guest favourite
Cabin in Wardensville
4.99 out of 5 average rating, 135 reviews

Sugar Maple Chalet - 67-Acre Farm

✔ Rustic Luxury: Cozy wood interiors, modern comforts, and charming decor. ✔ 67 Acres of Beauty: Private walking trails and historic outbuildings nestled in pristine nature. ✔ Stunning Views: Panoramic landscapes by day, stargazing by night. ✔ Modern Comforts: Well-appointed kitchen, high-speed Wi-Fi, and more. ✔ Outdoor Clawfoot Tub with shower: Relax under a maple tree—pure serenity when weather permits.

Top Guest favourite
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, 117 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 holiday rentals

When is the best time to visit Woodstock?

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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.

  • 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.

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

    Experience the best of Woodstock with our house rentals, starting at about $120 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 air conditioning?

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

  • 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.

Quick stats about holiday rentals in Woodstock

  • Total holiday rentals

    Explore 20 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $85 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Woodstock holiday 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