Holiday rentals in Woodstock

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Top-rated holiday rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 117 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.

Top guest favourite
A charming cabin is nestled among tall trees, illuminated by soft exterior lighting. The structure features a welcoming porch that extends around the building, while the sky transitions from twilight to dusk, creating a serene atmosphere.
Home in Rio
4.97 out of 5 average rating, 156 reviews

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!

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, 463 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.

Guest favourite
Two black Adirondack chairs are positioned on a grassy area next to the river, offering serene views of the water and surrounding trees. Gentle sunlight filters through the leaves, creating a peaceful atmosphere for relaxation.
Cabin in Woodstock
4.95 out of 5 average rating, 119 reviews

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.

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, 428 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, 588 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 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.
Guest house in Woodstock
4.97 out of 5 average rating, 159 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!!

Superhost
Cabin in Woodstock
4.89 out of 5 average rating, 121 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, 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 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.
Guest house in New Market
4.98 out of 5 average rating, 420 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 favourite
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, 129 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 favourite
A comfortable sleeping area features a spacious bed adorned with a patterned blanket and decorative cushions. A large wall tapestry depicting a serene moonlit scene complements the room. Nearby, a bedside table holds a lamp and decorative items, while artistic wall decorations add character.
Guest suite in Basye
4.91 out of 5 average rating, 115 reviews

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

Guest favourite
A cozy living room features a comfortable green sofa complemented by red chairs. Soft lighting is provided by table lamps on either side. Two windows allow natural light to fill the space, while decorative artwork and a clock enhance the inviting atmosphere.
Home in Edinburg
4.96 out of 5 average rating, 140 reviews

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

When is the best time to visit Woodstock?

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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
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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 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!

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