
Holiday rentals 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.

Mountaintop Cabin w/ Outdoor Tub
Come unwind at our mountaintop cabin! Whether it’s the (new cast iron) soaking tub on the back porch, the two hammocks, our giant firepit, or the comfy king bed in the loft, you’ll want to sit, sip, snuggle and tell tall tales as the sun sets and stars shine. Second small bedroom doubles as an office. A gas stove twinkles inside while an antique spiral staircase adds elegance. Fully-equipped kitchen, laundry, and Starlink to provide top-tier connectivity. We’re kid friendly and dog positive too!

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.

Rivah Retreat, HotTub~Firepit-Fishing-Deck-Private
Rivah Retreat is a one-of-a-kind luxury getaway tucked away on the pristine North Fork of the Shenandoah River. An expansive retreat and custom cabin spread over six acres of riverfront property located just 90 minutes from the White House. With a top-notch structure, modern amenities, hot tub, gas fireplace, spacious elevated deck, board games, movies, and so much more! Enjoy fly fishing from the private riverbank, quiet walks, abundant wildlife, smores at the outdoor firepit and relaxing.

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.

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!!

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, hot tub & seasonal indoor pool (cold plunge in the Winter!) ✓ Family-friendly w/ toys, games ✓ Near wineries, Shenandoah hikes & small towns

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.

Getaway Sweet Zen Suite at Bryce Ski and Bike Park
Beautiful basement apartment with WiFi, parking and walking distance to Bryce Ski and Bike park (1.5 mile walk), trails (Lake Laura is 1/2 mile walk) restaurants and bars (1/2 mile to nearest; 1.5 miles to the resort). Short drive to breweries/wineries (Swover Creek, Woodstock Brewery, Cave Ridge ) Bryce security patrols the area regularly. Additional hiking and biking within short drives. Microwave, coffee pot, toaster, mini frig in the unit

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

Homestead with Shenandoah Valley Views

Mountain & Lake Retreat: 2x Queen, saltH2O Hottub

Fully fenced modern farmhouse in Shenandoah Valley

Family Friendly Rancher w/ Large Fenced Yard

Dog-friendly historic home

10-7

Cozy Cabin in Fort Valley

The historic and charming Nicodemus House
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $182 SGD | $191 SGD | $169 SGD | $185 SGD | $185 SGD | $185 SGD | $184 SGD | $210 SGD | $176 SGD | $220 SGD | $216 SGD | $182 SGD |
| 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 $78 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Woodstock holiday rentals include wifi 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
- Bowling Green Country Club
- Dinosaur Land
- JayDee's Family Fun Center
- Warden Lake
- Doukénie Winery
- Blue Ridge Shadows Golf Club
- West Whitehill Winery
- Little Washington Winery
- Glass House Winery
- Car and Carriage Caravan Museum




