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...

Dec 8 – 15

ﺩ.ﺇ803 per night

Guest favorite

Cottage in Hamilton

4.94 out of 5 average rating, 309 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Nov 5 – 12

ﺩ.ﺇ851 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.

Jul 1 – 8

ﺩ.ﺇ952 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

ﺩ.ﺇ321 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!

Jul 15 – 22

ﺩ.ﺇ441 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

ﺩ.ﺇ664 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.

Mar 10 – 17

ﺩ.ﺇ451 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

ﺩ.ﺇ427 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.

Dec 21 – 28

ﺩ.ﺇ440 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.

Jan 6 – 13

ﺩ.ﺇ570 per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 186 reviews

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

Oct 2 – 9

ﺩ.ﺇ442 per night

Guest favorite

Cottage in Midland

4.97 out of 5 average rating, 129 reviews

The Stoney Cottage Hideaway

The Stoney Cottage is located on a 20 acre farm in the middle of beautiful Fauquier County. It provides a unique and peaceful getaway while still offering a lot of local attractions. It is conveniently located to many local attractions such as wineries, breweries, Farmers Markets, The Flying Circus air show, Civil War battlefields and the Shenandoah National Park.

Dec 23 – 30

ﺩ.ﺇ511 per night