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Woodstock vacation rentals

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Top-rated vacation rentals in Woodstock

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

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Tiny home in Quicksburg

4.99 out of 5 average rating, 211 reviews

Finn's Frolic-The place- relax, stay, or explore!

Finn's Frolic is our charming, new country tiny home. Less than 2 hours DC, Charlottesville. Beautiful farm, mountain views, deck, fire pit, charcoal grill, much more. Landscaping is in the works ! Kitchen is fully equipped, vintage & new dinner wear. Living room has an electric fireplace, huge picture window, comfy love seat. The bedroom is up traditional stairs: loft bedroom, 7 foot sloped ceiling. Great place to relax, base for visits to local wineries, attractions! Perfectly imperfect!

Guest suite in Woodstock

4.96 out of 5 average rating, 358 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.

Home in Edinburg

4.98 out of 5 average rating, 359 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.

Home in Edinburg

4.98 out of 5 average rating, 421 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.

Cottage in Maurertown

4.91 out of 5 average rating, 203 reviews

The Cottage at Little Ridge

The beauty of the Shenandoah Valley, the tranquility of a working family farm, and the delights of a taproom and cafe, all come together in this amazing property. This country modern one bedroom/one bath/kitchen unit is a brand new addition to Ridge Runner Farms. With its own private porch it offers views of this four acre working farm in Maurertown, VA. Ridge Runner also boasts a farm Cafe. Enjoy sunsets on your own porch or walk the 100 feet to enjoy a seat inside the welcoming cafe!

Guesthouse in Woodstock

4.96 out of 5 average rating, 108 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!!

Tiny home in Mount Jackson

4.96 out of 5 average rating, 260 reviews

Sacred Haven- "BIG" Tiny Home with Mountain View’s

Sacred Haven is an extraordinary custom built tiny home on wheels, not your typical tiny home. The spacious home features higher ceilings, custom wood ceiling and beams and 25 windows. A fantastic kitchen with bar counter. The bedroom has a walk-in closet with skylight to see the stars at night. The views are spectacular from any location and most enjoyable is the expansive deck with a large screened in porch off the side overlooking the pond, hay fields and mountains. NO PETS

Home in Edinburg

4.95 out of 5 average rating, 169 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.

Guesthouse in New Market

4.99 out of 5 average rating, 247 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.

Home in Woodstock

4.95 out of 5 average rating, 115 reviews

The Beckford House in Historic Woodstock

Welcome to the Beckford House! This charming house is nestled in Woodstock's historic district packed with character in every room. The view of the Blue Ridge Mountains over cow pastures from the back deck is quintessential Shenandoah Valley. The house is just a few minutes walk to a brewery, a bakery, an ice cream shop, the Woodstock Cafe, and scores of antique stores-- with award-winning wineries and breweries dotting the valley on both sides of the Shenandoah River.

Cabin in Lost River

4.96 out of 5 average rating, 136 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Guest suite in Woodstock

4.89 out of 5 average rating, 257 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Woodstock vacation rentals

Laptop-friendly workspace

Stay near Woodstock's top sights

Woodstock Brewhouse81 locals recommend

Muse Vineyards75 locals recommend

Woodstock Cafe61 locals recommend

Seven Bends State Park30 locals recommend

Flour & Water Co28 locals recommend

Woodstock Garden Cafe23 locals recommend

Other great vacation rentals in Woodstock

Home in Woodstock

4.94 out of 5 average rating, 51 reviews

Lovely fall views from Sue! New hot tub!

Home in Woodstock

4.77 out of 5 average rating, 26 reviews

Modernized historic farm house.

Cabin in Strasburg

4.93 out of 5 average rating, 15 reviews

A cabin getaway!

Home in Edinburg

4.88 out of 5 average rating, 58 reviews

Peaceful Retreat on Creekside

Home in Woodstock

4.97 out of 5 average rating, 58 reviews

Fully fenced modern farmhouse in Shenandoah Valley

Cabin in Woodstock

5 out of 5 average rating, 53 reviews

The Bird's Nest - Cabin by the River

Condo in Mount Jackson

4.97 out of 5 average rating, 68 reviews

Condo in Mount Jackson

Rental unit in Woodstock

4.93 out of 5 average rating, 14 reviews

The Roost at the Hen House

Quick stats about vacation rentals in Woodstock

Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

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 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.
How much does it cost to stay in house rentals in Woodstock?
Experience the best of Woodstock with our house rentals, starting at about $140 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 wireless internet?
Absolutely! We offer over 10 house rentals with wireless internet in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Woodstock?
Woodstock has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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