Cottage vacation rentals in Winchester

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Top-rated cottage rentals in Winchester

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Guest favorite

Cottage in Winchester

4.98 out of 5 average rating, 306 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...

Feb 10 – 17

R4,069 ZAR per night

Guest favorite

Cottage in Berryville

4.98 out of 5 average rating, 116 reviews

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.

Jun 30 – Jul 7

R4,808 ZAR per night

Guest favorite

Cottage in Strasburg

4.98 out of 5 average rating, 106 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.

Jan 12 – 19

R3,040 ZAR per night

Guest favorite

Cottage in Winchester

4.9 out of 5 average rating, 101 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

Sep 15 – 22

R1,620 ZAR per night

Guest favorite

Cottage in Maurertown

4.92 out of 5 average rating, 194 reviews

The Cottage at Little Ridge

The beauty of the Shenandoah Valley, the tranquility of a working family farm, and the delights of a taproom and cafe, all come together in this amazing property. This country modern one bedroom/one bath/kitchen unit is a brand new addition to Ridge Runner Farms. With its own private porch it offers views of this four acre working farm in Maurertown, VA. Ridge Runner also boasts a farm Cafe. Enjoy sunsets on your own porch or walk the 100 feet to enjoy a seat inside the welcoming cafe!

Jun 5 – 12

R2,223 ZAR per night

Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 367 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Jan 30 – Feb 6

R2,014 ZAR per night

Guest favorite

Cottage in Fort Valley

4.96 out of 5 average rating, 159 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.

Dec 12 – 19

R3,353 ZAR per night

Guest favorite

Cottage in Gordonsville

5.0 out of 5 average rating, 127 reviews

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Apr 19 – 26

R2,844 ZAR per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Dec 12 – 19

R2,277 ZAR per night

Guest favorite

Cottage in Warrenton

4.97 out of 5 average rating, 264 reviews

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Aug 13 – 20

R2,156 ZAR per night

Guest favorite

Cottage in Timberville

4.92 out of 5 average rating, 456 reviews

Cider House Orchard Stay

Welcome to the Old Hill Cider House at Showalter's Orchard! Located just steps away from the first row of Summer Rambo Apple Trees at Showalter's Orchard. The thoughtful renovation was only completed in early July. The former wash house could be a base for all your Shenandoah Valley Travels, or this light, airy and romantic little house is a comfortable and cozy place for your farm vacation.

Nov 11 – 18

R2,222 ZAR per night

Superhost

Cottage in Front Royal

4.91 out of 5 average rating, 340 reviews

Mountain View with pond/cottage in front royal VA

Nestled on a beautiful family farm that has view of 3 mountains and a pond that is stocked for fishing. Access to the Shenandoah River, 3 miles from skyline drive, great shops on main street front royal and old rag is close by and skyline caverns. Come see us and please let us know any allergies as we leave fresh baked muffins. We have Xfinity high speed wireless internet connection.

Mar 24 – 31

R2,689 ZAR per night