
Cottage holiday rentals in Winchester
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Top-rated cottage rentals in Winchester
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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...

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!

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

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit
Moonflower Cottage is a historical farmhouse nestled on two rolling acres in Virginia's wine country. Visit the area's top vineyards, dining, and antique shops. Float down the Shenandoah River. Cap your day sipping cabernet as the sun sets and the cottage blooms like the moonflowers that grow wildly. Bathe in the warm glow of string lights under the grapevine arbor or enjoy a relaxing soak in the spa. Young or old, you are sure to find the vintage that you are looking for at Moonflower Cottage.

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!

Guest Cottage on Historic Estate & Cattle Farm
Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

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.

The River House
A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

Modern, private cottage at Fairview Organic Farm
Discounts for stays of 5 nights or more. Sitting atop a hill on 23 acres at historic Fairview Organic Farm, Circa 1737, the newish cottage is surrounded by pasture, organic gardens, history & overlooks the Harpers Ferry Gap. We are just a few miles from Charles Town, Harpers Ferry, Shepherdstown, the Hollywood Casino, the Appalachia trail, the Shenandoah & Potomac Rivers, and many historical sites. Enjoy sun rise from the deck and sunsets from the porch.

Emma's Stone Cottage
Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

The Creekside Cottage: Downtown | Pet-Friendly
Welcome to the Creekside Cottage, a 2 bedroom/1.5 bathroom spacious home, offering a secluded escape by the creek yet just a short stroll through the gardens of Shepherdstown to shopping and dining. Perfect for getaways, family visits, or university stays, this Creekside Cottage offers a roomy interior, cozy living room, modern kitchen, fire pit, and a private patio & porch to be enjoyed along the Town Run.

Snickers Gap Cottage
Historic cottage nestled in the foothills of the Blue Ridge Mountains, minutes from multiple breweries, wineries, hiking and biking trails, and the Shenandoah river. At just 40 miles west of Washington DC it’s the perfect weekend getaway to the country! We are known for our miles and miles of beautiful country roads. Come spend a weekend (or more!) and get lost in Loudoun.
Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub

Holly Tree Retreat Located In Beautiful Luray, VA.

Cozy Cottage in the heart of Berkeley Springs WV

*Cottage @ Firefly Cellars* VA Wine Country escape

Vibrant Cottage | Hot Tub | Pets | Shenandoah NP

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

THE PERFECT HIKING & WINERY COUNTRY RETREAT

Mountain Meadow Cottage w/ Hot tub & Mt Views

Shenandoah River Retreat
Pet-friendly cottage rentals

Hilltop Cottage @ Shiloh

Muse Vineyards Farmhouse, w Seasonal Pool!

Lakeside Retreat! Coffee bar, fire-pit, stargaze!

The willow tree house

Robins Nest

Garden Oasis outdoor entertainment at FrogPointe.

The Cottage at Old Salem School

Sweet Grass Cottage pond dock fire pit
Private cottage rentals

Riverfront Cottage in Shepherdstown, WV

Avery Pines Cottage

Modern 3BR Farmhouse in the Country

Wheatland Spring Farm + Brewery Cottage House

Bridge House, 10 min to Shen. Nat'l. Park

House/cottage 2bed, Private yard, walk to Oldtown

The Soper House-A Quaint & Lovely Country Getaway

C&O Canal/Potomac River Lock Keepers Cottage
Quick stats about cottage rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $248 NZD per night before taxes and fees

Verified guest reviews
Over 40 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
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- Cottage rentals Virginia
- Cottage rentals United States
- Whitetail Resort
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Cunningham Falls State Park
- Berkeley Springs State Park
- Cacapon Resort State Park
- Gambrill State Park
- South Mountain State Park
- Harpers Ferry National Historical Park
- Shenandoah River Outfitters
- Sky Meadows State Park
- Jiffy Lube Live
- Big Cork Vineyards
- Cooter's Place
- Green Ridge State Forest
- Antietam National Battlefield
- Reston Town Center
- Rock Gap State Park
- Museum of the Shenandoah Valley
- Old Town Winchester Walking Mall
- Bluemont Vineyard
- Catoctin Mountain Park
- Greenbrier State Park




