Cottage holiday rentals in Woodstock

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Top-rated cottage rentals in Woodstock

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Guest favourite
An outdoor fire pit surrounded by Adirondack chairs is situated on a stone patio, providing a cozy gathering space. A custom pavilion with string lighting is visible in the background, along with a garage that features amenities for leisure activities.
Cottage in Basye
4.92 out of 5 average rating, 101 reviews

HotTub | FirePit | GameRoom | .5mi to resort l 4BR

The Hideaway blends the best of Bryce Mountain with a stylish, professionally designed retreat. Just half a mile from Bryce Resort, you’re minutes from skiing, tubing, hiking, mountain biking, and golf—then back to modern comfort when the day’s adventures are done. *Keyless entry *Hot Tub with string lighting *Fully loaded game room in outdoor garage - complete with foosball, ping pong, Arcade, TV, and Darts. *Fire pit *Hi-Speed Wi-Fi (600 MBPS) *Fireplace *SMART TV's - includes YouTube TV

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, 434 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 favourite
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, 135 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 favourite
A spacious deck offers unobstructed views of rolling hills and valleys, accented by vibrant autumn foliage. The sky is expansive, displaying soft clouds and blue tones. A sleek railing encircles the deck, enhancing the serenity of the natural landscape.
Cottage in Markham
4.96 out of 5 average rating, 167 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 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, 116 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, 127 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, 106 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, 102 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
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, 200 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 !

Top guest favourite
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, 553 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, 226 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.

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, 282 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.

Popular amenities for cottage rentals in Woodstock

Quick stats about cottage rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $169Ā SGD per night before taxes and fees

  • Verified guest reviews

    Over 250 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!

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