Cottage holiday rentals in Winchester

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...

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!

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.

C&O Canal/Potomac River Lock Keepers Cottage

Located just steps away from Dam #4 on the C&O Canal / Potomac River. (marker 84.6) Perfect for a getaway or romantic weekend. Hike/bike the C&O Canal, bring your kayak/canoe/bikes, fish or swim in the river. Sit on the porch and listen to the rumble of the water falling over the dam. Local lore is this was the home of a canal lock keeper or the gate house keeper. Secluded location away from town. NOT A PARTY HOUSE/owner on site in garage apartment. Inquire if a blocked day is available.

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.

NEW * The Getaway Cottage at Rocky Marsh Farm

Welcome to The Getaway Cottage, a charming two-bedroom, two-bath home nestled in a peaceful country setting, located just 3.5 miles from Shepherdstown. Our location offers easy access to all the exciting activities and attractions the eastern panhandle has to offer, enjoy a short country side drive to dining, shopping, hiking trails, white water rafting and kayaking adventures. The historic town of Harpers Ferry is a short 25-minute drive away, and 15 minutes to Antietam Battlefield.

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.