
Holiday houses in Woodstock
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Top-rated holiday rentals in Woodstock
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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!

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.

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!!

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.

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.

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

Studio along i81: Near Wine, Beer, Hiking & Nature
Newly renovated detached studio guest-suite located in the beautiful Shenandoah County with country feels and easy access to I81. It features a butcher block bar for eating/working, a queen size bed, tv with Netflix along with Chromecast so you can cast your favorite shows from your phone/laptop, and during the summer you'll have the quietest and smart ac unit on the market. It has a shared driveway with the host's primary residence.

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.
Popular amenities for Woodstock holiday rentals
Other great holiday rentals in Woodstock

Family Friendly Rancher w/ Large Fenced Yard

Near River, Family-friendly, WiFi, Veteran owned!

Rustic French Getaway •King Bed•Near Cavern

The historic and charming Nicodemus House

Escape to the Shenandoah River

The Suite @Wine and Country Inn

Historic home w/ firepit, grill, all seasons porch

Cozy Tiny Home Retreat on Shenandoah Valley Farm
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $243 NZD | $255 NZD | $225 NZD | $246 NZD | $246 NZD | $246 NZD | $244 NZD | $279 NZD | $234 NZD | $293 NZD | $288 NZD | $243 NZD |
| 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.
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 holiday rentals in Woodstock

Total holiday rentals
Explore 20 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $104 NZD per night before taxes and fees

Verified guest reviews
Over 2,400 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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- Timberline Mountain
- Luray Caverns
- Stone Tower Winery
- Early Mountain Winery
- Shenandoah Valley Golf Club
- Bryce Resort
- Cacapon Resort State Park
- Creighton Farms
- Robert Trent Jones Golf Club
- Massanutten Ski Resort
- Prince Michel Winery
- Notaviva Vineyards
- Sly Fox Golf Club
- Dinosaur Land
- Bowling Green Country Club
- JayDee's Family Fun Center
- Warden Lake
- West Whitehill Winery
- Blue Ridge Shadows Golf Club
- Doukénie Winery
- Little Washington Winery
- Glass House Winery
- The Car and Carriage Caravan Museum
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