Cottage holiday rentals in Woodstock

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Top-rated cottage rentals in Woodstock

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Top Guest favourite
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, 457 reviews

COZY+SEXY 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...

Guest favourite
The charming cottage is nestled on a grassy area, framed by trees. A welcoming front porch and steps lead to the entrance. Two outdoor firepits can be seen nearby, providing cozy spots for gatherings under the evening sky.
Cottage in Mount Jackson
4.92 out of 5 average rating, 113 reviews

Hot Tub!, 2 Fire Pits, Huge Deck, Private orchard!

The home is an adorable cottage perfect for both a romantic getaway or a family/friends retreat. Enjoy views of the small orchard on the 3 acre wooded property from the large deck and two firepits. The Orchard Cottage is a great base to explore local wineries, hiking, and nearby Bryce Resort. Conveniently located 2 hrs from DC, 45 minutes from Harrisonburg, and only 12 minutes from Bayse/Bryce Ski Resort. Only a 15 min drive to I-81 to conveniently access all the Shenandoah Valley has to offer

Top Guest favourite
A new cottage is set against the backdrop of rolling hills and mountains, featuring a metal roof and welcoming porch. A hot tub is positioned on the patio, while a gravel path leads up to the house, surrounded by open farmland with a sunset in the distance.
Cottage in Elkton
4.99 out of 5 average rating, 199 reviews

Shenandoah River Retreat

New guest cottage with gorgeous view of the Massanutten and Blue Ridge Mountains, access to the South Fork of the Shenandoah River. Sit on the porch and soak it all in, enjoy the river, and local activities King size bed, gas range/fireplace, all new appliances Wi-Fi and TV for local stations and Roku. Surrounded by farm land, bucolic setting. 4.5 miles from Merck, 2.5 miles from Coors, 3.5 miles from Massanutten Resort, 14 miles to Shenandoah National Park, 13 miles to JMU. No pets or smoking

Top Guest favourite
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, 132 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 favourite
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, 128 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 favourite
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, 111 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 favourite
The modern cabin is framed by lush greenery, showcasing a unique combination of wood and metal siding. A circular fire pit surrounded by black adirondack chairs is situated in a gravel area, leading to a pathway that connects to the entrance of the cabin.
Cottage in Lost City
4.98 out of 5 average rating, 108 reviews

Hidden Hideaway

Welcome to your retreat, your Hidden Hideaway. Leave the hustle and bustle of the city to relax and rejuvenate in Lost River. This luxury minimalist cabin has everything you want and need whether you are looking for a quick weekend getaway or a month-long working vacation. Immerse yourself in nature on the screened in porch, gaze into the Milky Way stars as you sit around the fire pit, or curl up with a book in the sun drenched reading nook, you will find what you need at Hidden Hideaway.

Top Guest favourite
A charming cottage with a steeply pitched roof is surrounded by a tranquil winter landscape. Fresh snow covers the ground, and soft flakes fall gently, contrasting with the dark wood exterior. The entrance features a decorative door, framed by colorful window accents.
Cottage in Bentonville
4.97 out of 5 average rating, 564 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.

Top Guest favourite
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, 240 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 favourite
A single-story cottage features a red metal roof and light-colored exterior. Situated on a spacious lawn, the front porch is accessorized with white railings. The backdrop showcases rolling green hills and a distant mountain under a clear sky.
Cottage in Luray
4.97 out of 5 average rating, 397 reviews

Holly Tree Retreat Located In Beautiful Luray, VA.

Welcome to Holly Tree Retreat located in the heart of the Shenandoah Valley, nestled between the Blue Ridge and Massanutten Mountains in Luray, VA. We're within walking distance of Cooter's, 10 minutes away from everything that downtown Luray has to offer with restaurants, brewery, theater, shopping and live entertainment. Holly Tree Retreat is just minutes away from Shenandoah National Park, Luray Caverns, Shenandoah River, George Washington National Forest and Skyline Drive.

Guest favourite
A modern living area features a sleek brown sofa adorned with green and cream pillows. Light wood flooring complements the minimalist decor, while a round table with chairs is positioned nearby. The kitchen is visible in the background, showcasing clean lines and bright surroundings.
Cottage in Timberville
4.94 out of 5 average rating, 300 reviews

Raven Ridge Retreat: Romantic Orchard Getaway

Raven Ridge Retreat sits amidst our Granny Smith & Gala Apple Trees at Showalter's Orchard, home of Old Hill Cidery. This light-filled, recently-constructed cottage highlights extraordinary views of The Massanutten and the Blue Ridge Mountains, the Shenandoah Valley, rows and rows of apple trees, and abundant wildlife. This two-story, romantic farm stay is base for all your area adventures like hiking in Shenandoah National Park or exploring The Shenandoah Spirits Trail.

Guest favourite
A serene landscape is captured at dusk, showcasing sweeping fields with hints of frosted ground. Majestic mountains are visible in the distance, highlighted by the warm hues of a vibrant sunset, blending shades of orange and pink against the evening sky.
Cottage in Shenandoah
4.94 out of 5 average rating, 210 reviews

Cozy Cottage Retreat: SNP, Luray Caverns, River

Clean & cozy cottage conveniently located in the town of Shenandoah. Guest love the central location to Shenandoah National Park via Elkton Swift Run (12 miles) or Luray Thornton Gap (28 miles), Luray Caverns (15 mi), Massanutten Resort (9 mi), and a short drive to local colleges like JMU, EMU, and Bridgewater College. Walking distance to Shenandoah River, a public boat landing, local stores and small parks. Please check out our reviews to see what guest have to say.

Popular amenities for Woodstock cottage rentals

Quick stats about cottage rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $184 AUD per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodstock rentals

  • 5 Average rating

    Woodstock stays are highly rated by guests—averaging 5 out of 5!