
Holiday houses in Woodstock
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Top-rated holiday rentals in Woodstock
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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.

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

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.

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.

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.

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.

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.

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.

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

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.

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.

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
Other great holiday rentals in Woodstock

CloudPointe Retreat

Tangled Up in Blue Cabin w/ Hot Tub + Firepit

Bear Cave-Bryce passes/lift tkts/32 Acr/Gym/Sauna/

A Cabin Hideway

Bald Eagle Cabin at Buffalo Gap Retreat

The historic and charming Nicodemus House

Cozy Cabin in Fort Valley

The Woodstock (VA) Hippie House
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $198 AUD | $208 AUD | $184 AUD | $201 AUD | $201 AUD | $201 AUD | $199 AUD | $228 AUD | $191 AUD | $232 AUD | $199 AUD | $195 AUD |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 13°C | 16°C | 18°C | 18°C | 15°C | 9°C | 4°C | -1°C |
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!
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- Shenandoah National Park
- Timberline Mountain
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Early Mountain Winery
- Cacapon Resort State Park
- Prince Michel Winery
- Jiffy Lube Live
- Glass House Winery
- Shenandoah River Outfitters
- Sky Meadows State Park
- James Madison University
- Cooter's Place
- Bluemont Vineyard
- White Lotus Eco Spa Retreat
- Grand Caverns
- James Madison's Montpelier
- Skyline Caverns
- Museum of the Shenandoah Valley
- Massanutten Indoor WaterPark
- Shenandoah Caverns
- Old Town Winchester Walking Mall
- White Oak Lavender Farm & The Purple WOLF Vineyard




