
Cottage holiday 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.

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...

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

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!

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

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.

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.

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.

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.

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.

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.

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.

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
Cottage rentals with a hot tub

Glade Cottage at White Lotus Eco Spa Retreat

Round House w Mountain View | Hot Tub

Riverfront Tree House- Ski, Sauna, Hot Tub, Arcade

Creekside Cottage at Shenandoah

Mountain Getaway – Hot Tub, River, Foosball & Ski

THE PERFECT HIKING & WINERY COUNTRY RETREAT

Cottage at Lost River Ridge

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit
Pet-friendly cottage rentals

Willie's Place Country Cottage Pets Allowed

Mountain Escape, Coffee Bar, Lake, Pool, Fish

Private Fenced Yard for Dogs/Horses - 2BR Cottage

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

The Cottage at Old Salem School

Spectacular Mountain Retreat

Amy's Place

Sweet Scenes Cottage
Private cottage rentals

Cottage on Trout Stream, 70+ acres & EV Charger

Maple Cottage - Cheery Ridgetop Home in Mt Jackson

Hebron Valley Sunsets Cottage

Cozy Cottage

Old Rag Cottage - sunny 2 bedroom near everything

Cozy and charming. Large covered deck & firepit.

Willow Wind Cottage

Cottage on the Knob. Cheerful one bdrm w/fire pit.
Quick stats about cottage rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $167 SGD 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Western North Carolina Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Shenandoah National Park
- Timberline Mountain
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Early Mountain Winery
- Cacapon Resort State Park
- Prince Michel Winery
- Jiffy Lube Live
- Glass House Winery
- James Madison University
- Sky Meadows State Park
- Shenandoah River Outfitters
- Grand Caverns
- White Lotus Eco Spa Retreat
- Cooter's Place
- Bluemont Vineyard
- James Madison's Montpelier
- Skyline Caverns
- Museum of the Shenandoah Valley
- Shenandoah Caverns
- Hollywood Casino At Charles Town Races
- Old Town Winchester Walking Mall
- White Oak Lavender Farm & The Purple WOLF Vineyard




