Cottage vacation rentals in Woodstock

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Top-rated cottage rentals in Woodstock

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Top guest favorite

A spiral staircase ascends beside a cozy living area adorned with large windows, allowing ample natural light. A dark sofa is positioned for relaxation, while a dining table nearby invites gatherings. Thoughtful decorative elements, including wall art and greenery, enhance the inviting ambiance.

Cottage in Locust Grove

4.99 out of 5 average rating, 136 reviews

Quaint & Cozy LakeView Cottage - Lake of the Woods

Welcome to Brent and Carla's Lake View Cottage! Our beautifully renovated, fully furnished, unique and luxurious home is stocked with everything you need to enjoy your stay in beautiful Lake of the Woods. Our cozy cottage is a perfect get-away for your next vacation, visit with family, work trip, staycation or weekend getaway. You will instantly be set at ease as you enter our home featuring wonderful décor, detailed craftsmanship and lots of amenities to make your stay relaxing and memorable.

Guest favorite

A spacious outdoor deck offers sweeping views of the surrounding trees and distant hills. Large glass sliding doors provide access to the interior, enhancing the connection between indoor and outdoor spaces. The deck features a wooden floor, contributing to a natural ambiance.

Cottage in Markham

4.96 out of 5 average rating, 140 reviews

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Top guest favorite

A serene outdoor space features a gently flowing water feature surrounded by lush greenery and varied stones. Two red Adirondack chairs are positioned for relaxation, overlooking the tranquil landscaping. The scene is set amidst a shaded area, inviting moments of peace and nature appreciation.

Cottage in Stanardsville

4.98 out of 5 average rating, 233 reviews

The Birds Nest Cottage

Our home is a newly renovated charming cottage nestled in the foothills of the beautiful Virginia Blueridge Mountains. You'll enjoy old cottage charm with added modern but classic updates to the entire home. Relax on the screened in back porch with tranquil sound of a water feature . Our home is centrally located near several beloved attractions like Skyline drive, Charlottesville, Massanutten Ski Resort, wineries and antique shops. Greenehills Country Club is directly across from our home.

Guest favorite

Cottage in Shenandoah

4.97 out of 5 average rating, 204 reviews

Charming Cottage in the Heart of Shenandoah!

Cozy & inviting cottage less than 1 mile from public access to the Shenandoah River. Many attractions nearby: Shenandoah National Park, Massanutten Four Seasons Resort, Luray Caverns, George Washington National Forest, Lake Arrowhead and more! Enjoy tubing, canoeing, kayaking or fishing by visiting Shenandoah River Adventures (less than 1 mile away). Whether you are looking for outdoor adventures or a secluded getaway, this home offers all the amenities you'll need to have an enjoyable trip.

Guest favorite

A outdoor gathering area features five gray Adirondack chairs arranged around a stone fire pit. The surrounding area displays grassy grounds with fallen leaves and a backdrop of trees, some with autumn foliage. A gentle slope leads down to a small creek nearby.

Cottage in Madison

4.91 out of 5 average rating, 139 reviews

Creekside Cottage Near Hiking

Creekside Cottage is the perfect getaway home to escape to the beautiful Blue Ridge Mountains. This newly renovated luxury cottage is only minutes from hiking trails and just a short drive from the Old Rag trailhead. Nestled in Syria, Virginia, this comfortable space features updated amenities such as a rain shower, a well appointed kitchen, plenty of lounge spaces, board games for days, and a central wood burning stove. Just a few steps out the back door you'll find your own private creek.

Guest favorite

Cottage in Round Hill Village

4.93 out of 5 average rating, 184 reviews

Best Countryside Retreat & No Cleaning Fees EVER

Luxurious & cozy cottage, nestled in Virginia's wine country. With a gas fireplace, amazing beds & linens, gourmet kitchen with EVERYTHING and the great hospitality of owners Jennifer and Eric, you will have a premier visit! Self check in anytime and we are on the 26 acre property for 24/7 service. Beautiful vistas, wineries, and activities, over 200 five-star reviews (Airbnb& VRBO) max privacy and convenience. Relax in our tranquil setting while enjoying all the delights of the region!

Guest favorite

Cottage in Bluemont

4.95 out of 5 average rating, 240 reviews

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May1- Sept 14. PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

Guest favorite

A cozy cottage is set against a backdrop of rolling hills, with a large tree and string lights enhancing the outdoor area. A fire pit is surrounded by chairs, while a picnic table invites outdoor meals. A hammock is visible in the background, creating a peaceful retreat.

Cottage in Crozet

4.91 out of 5 average rating, 173 reviews

Idyllic Cottage Retreat

Kick back and relax in this 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 front porch is showcased, featuring two white rockers positioned on a wooden deck. The scene is enhanced by a misty landscape in the background as the sun rises over rolling hills, casting a soft light on the surroundings.

Cottage in Gordonsville

5 out of 5 average rating, 167 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.

Top guest favorite

Cottage in New Market

4.98 out of 5 average rating, 128 reviews

Lakeside, fishing, fire pit, swimming, coffee bar

PET FRIENDLY Come experience Reel and Relax!! Hike, explore the trails, fish, float, go rafting, read, enjoy a fire, grill, shop/eat in super cute country towns... Whether its the river, the rolling mountains, the whispering breeze or the cozy cottage, this property offers all of the feels you are searching for without ever leaving! Every season is magical and offers its own reason to visit!!! "This place is amazing; you have literally thought of EVERYTHING! -past guest.

Top guest favorite

The exterior of Rose Cottage is surrounded by lush blooming flowers, creating a colorful welcome. A white picket fence borders the entrance, leading to a rustic wooden door framed by a trellis. Sunlight filters through the green foliage overhead, accentuating the charming garden setting.

Cottage in Sperryville

4.98 out of 5 average rating, 117 reviews

Adorable Rose Cottage in Village of Sperryville

Rose Cottage is a quaint one-of-a-kind retreat in the heart of Sperryville - a charming country village offering shops, galleries, eateries, and more. The property has an excellent location, only 1.5 hours from Washington, DC and convenient to Culpeper, Warrenton, Front Royal and Interstate 66. It is approximately 15 miles from Old Rag Mountain and a 15 minute drive to the Shenandoah National Park, which offers an amazing array of waterfalls, canyons, trails, and hikes.

Top guest favorite

The charming exterior of the cottage is shown, featuring a light-colored facade with multiple windows. A welcoming front door is visible, surrounded by vibrant flowers and greenery. A small stone walkway leads to a patio area with wooden seating, overlooking the lush yard.

Cottage in Bluemont

4.96 out of 5 average rating, 207 reviews

The Cottage at Stonecroft

Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.