Cottage vacation rentals in Woodstock

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Woodstock

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.

Cottage in Winchester

4.99 out of 5 average rating, 419 reviews

Uber SXY Private Country Escape! Hot Tub & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Top guest favorite

A fire pit surrounded by multiple Adirondack chairs sits on a gravel surface. The backyard vegetation includes trees and shrubs, while a grey house with lit windows is visible in the background, complementing the serene outdoor setting.

Cottage in Wardensville

4.99 out of 5 average rating, 123 reviews

Cottage at Lost River Ridge

"This is a beautiful house and the perfect peaceful weekend getaway." -Guest With a hot tub, king beds, complimentary firewood, fully equipped kitchen, and 75-inch TV for movie night, this is the secluded mountain oasis you've been dreaming of for that much-needed getaway! When you're not roasting smores over the fire, or soaking in the hot tub, take a trip into town and experience local gems like a bustling farmer's market, tasty eateries, charming shops, and a wealth of outdoor activities!

Guest favorite

The exterior of the Sunrise Cottage is showcased amidst colorful autumn foliage. The single-story home features a green roof, spacious front lawn, and a gravel driveway. Mature trees frame the property, enhancing the peaceful rural setting.

Cottage in Fort Valley

4.94 out of 5 average rating, 203 reviews

Cozy Cottage - HOT TUB | Mountain Views | Pets

Welcome to the Sunrise Cottage! Stay here if you want a secluded retreat in nature, easy access to hiking trails, gorgeous views & charming towns. Listen to the sounds of the farm animals while you relax in the hot tub or on the enclosed porch. Beautifully decorated with a fire pit and grill. Within 30 mins from all the major attractions that the Shenandoah Valley offers like Luray Caverns, Shenandoah National Park, Vineyards. Perfect retreat for some R&R away from the city! BOOKING FOR SUMMER!

Guest favorite

A charming cottage exterior showcases a green facade with textured wood siding, complemented by a welcoming porch. Outdoor seating is provided by rustic chairs around a fire pit on the lawn. A table nearby offers an inviting spot for dining, set against a backdrop of distant mountains.

Cottage in Crozet

4.91 out of 5 average rating, 190 reviews

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Top guest favorite

A rustic white cottage is featured alongside a glass greenhouse, both set under a blue sky with scattered clouds. Lush greenery surrounds the buildings, and a stone birdbath is visible in the garden area, enhancing the natural charm of the setting.

Cottage in New Market

4.99 out of 5 average rating, 104 reviews

The Cottage at B and M Journey Farm

Take it easy at this unique and tranquil getaway. The Cottage at B and M Journey Farm is rustic and cozy and placed on a working farmette. Enjoy evening walks through pollinator spaces and the vineyard. Rise with the sunrise over New Market Gap and settle in at the fire pit overlooking the vineyard. In cooler months enjoy the cabin’s gas fireplace (if you wish). Hiking trails are nearby on New Market Mountain or the Shenandoah National Park. Food and wineries may be found within a short drive.

Top guest favorite

A serene outdoor scene features a gravel pathway leading to a small structure made of stone. A stack of firewood is neatly arranged nearby, with a wheelbarrow positioned in the foreground. Lush greenery surrounds the area, offering a view of the calm river in the background.

Cottage in Strasburg

4.98 out of 5 average rating, 122 reviews

Shenandoah Riverfront - Happy Peach Cottage

Come relax at The Happy Peach! Nestled at the base of the Massanutten Mountains on the North Fork of the Shenandoah River (100 feet of frontage), this cozy house is the perfect base for adventures or a restful getaway. Fishing, hiking, rafting, antique shopping, wine tasting, caverns & historic sites are some options. Our 2-bedroom house is an ideal getaway for a small group or family and only a 90-minute drive from DC. And, there's high-speed fiber optic internet for to stay connected.

Top guest favorite

A spacious outdoor patio area is visible, featuring seating arranged for relaxation. Trees line the bank of the river, with open fields on the opposite side. The clear water reflects sunlight, and the mountains are visible in the background under a bright blue sky.

Cottage in Woodstock

4.99 out of 5 average rating, 100 reviews

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.

Top guest favorite

The exterior of the cottage is captured from an angle, showcasing its charming two-story structure with a sloped metal roof. Lush green hills rise in the background, while a grassy area with trees surrounds the property, providing a serene natural setting.

Cottage in Mathias

4.93 out of 5 average rating, 197 reviews

Lost River Dog/Bike friendly 3BR/2BA-large deck

This classic family-friendly cottage in Lost River is sure to warm your heart with 3 BD/2 full bath, fenced-in yard, heated bath floors, 9 ft ceilings and comfortable furniture provides a lodge ambiance and a wonderful place to relax. Pet friendly with large fenced in yard and a large "treehouse" deck with table, Adirondack chairs, large propane gas grill and a reverse osmosis filter at kitchen sink for the best drinking water. Bike & gravel friendly. Ask us about Lost River routes !

Guest favorite

A two-story cottage is set amidst a wooded backdrop, showcasing a mixture of wood and stone exterior. Large windows and a balcony enhance the home’s charm. A pathway leads to the entrance, and a few outdoor seating options are visible on the lower level.

Cottage in Bentonville

4.97 out of 5 average rating, 541 reviews

The Cottage

Need some time to refresh? Spending time in the foothills of the Skyline Drive at our cozy cottage may be for you. Well behaved dogs are welcome but not on furniture. The driveway is long and home is very secluded. Winter access will be subject to weather conditions. Driveway does not get plowed and gets rutty during rainy periods. Cell service is spotty on Browntown road. The cottage has a landline and wifi. Use your wifi calling feature for cell phone use. More info under photos.

Guest favorite

An airy living room features a large sectional sofa with decorative pillows, a wooden TV stand with a small television, and a scenic view through French doors. Light-colored curtains frame the doors, and a soft area rug with a subtle pattern lies on the hardwood floor.

Cottage in Timberville

4.95 out of 5 average rating, 257 reviews

The Orchard Oasis: Charming & Romantic Farm Stay

Welcome to our Orchard Oasis, steps away from the Granny Smith & Gala Apple Trees at Showalter's Orchard, home of Old Hill Cidery. We built this light-filled, romantic aerie to highlight extraordinary views of The Massanutten and the Blue Ridge Mountains, The Shenandoah Valley, rows and rows of apple trees, and abundant wildlife, all from your front porch. The two-story cottage could be a base for all your Shenandoah Valley Travels or a comfortable and cozy place for your farm vacation.

Guest favorite

Two dogs are seated on black chairs in a grassy area, facing a charming cottage with a stone chimney. The house, featuring numerous windows, is surrounded by a spacious wooden deck. A fire pit is visible in the foreground, providing a cozy gathering spot.

Cottage in Fort Valley

4.96 out of 5 average rating, 220 reviews

Cozy Cottage/Pet Heaven

Deep breath...exhale. Looking for the perfect place to hideaway? You have found it. Enjoy big skies, picturesque landscapes, friendly farm animals and colorful sunsets. Nestled in the valley within the valley, you are surrounded by the George Washington National Forest. Offering hiking, biking, ATV trails, and so much more. Skyline Drive and Luray Caverns are just a 30 min drive. 30 minutes to shopping. Located less than 2 hours west of DC. Come see what you have been missing.

Top guest favorite

A view from an open doorway reveals a covered porch with white rocking chairs. A welcome mat lies on the wooden floor, leading to a scenic landscape of rolling hills adorned with autumn foliage. A glimpse of black chairs is visible in the distance.

Cottage in Gordonsville

5 out of 5 average rating, 179 reviews

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.