Vacation rentals in Ridgeway

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Top-rated vacation rentals in Ridgeway

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Guest favorite

Guest suite in Summit Point

4.97 out of 5 average rating, 129 reviews

The Big Room - Historic Schoolhouse

Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. There are even a couple sidewalks ;) We have 3 churches and a post office. The "Railside Market" serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia!

Jan 18 – 25

G$26,394 GYD per night

Guest favorite

Farm stay in Round Hill

4.94 out of 5 average rating, 347 reviews

Come and get your goat on!

Nestled at the base of the Blue Ridge and tucked away in the woods, we offer a quiet and peaceful get away while being convenient to tons. Enjoy the peace of 13-acres of woodlands and pasture. A large private deck provides a plenty sun with pasture and woodlands views with some great star watching at night. Miles of walking, the Appalachian trail, fantastic cycling; historic towns and places; wineries, breweries, and distilleries; Potomac and Shenandoah rivers. All just minutes away.

Aug 17 – 24

G$26,972 GYD per night

Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 138 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Jul 21 – 28

G$34,431 GYD per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 547 reviews

Arden House, Inwood WV

Ground level studio apartment. No steps. Completely separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed and sofa. In a separate living area, there is a queen bed, TV, private bath, desk, table, microwave, convection oven, air fryer, refrigerator Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

Jan 25 – Feb 1

G$17,844 GYD per night

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 272 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

Aug 16 – 23

G$31,649 GYD per night

Guest favorite

Cabin in Paw Paw

4.96 out of 5 average rating, 175 reviews

Easygoing

Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with lots more room to spare, indoor toilet but BEST of all is showering outside!

Jun 25 – Jul 2

G$20,675 GYD per night

Guest favorite

Home in Winchester

4.98 out of 5 average rating, 152 reviews

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

Jan 13 – 20

G$30,464 GYD per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 424 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.

Jun 11 – 18

G$25,597 GYD per night

Guest favorite

Cabin in Lost River

4.96 out of 5 average rating, 112 reviews

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Mar 19 – 26

G$20,195 GYD per night

Guest favorite

Townhouse in Winchester

4.95 out of 5 average rating, 171 reviews

Modern Elegance in Historic Old Town Winchester

Just a block and a half from the Old Town Winchester pedestrian mall, this historic beauty with modern elegance is sure to please. You are within walking distance of quaint shops, great restaurants, The Brightbox Theater, and The Shenendoah Discovery Museum. Spend the day touring the areas great wineries or enjoying Skyline Drive, and then return to enjoy a great night out, or an evening at home making dinner in the spacious modern kitchen.

Oct 18 – 25

G$23,458 GYD per night

Guest favorite

Cabin in Shepherdstown

4.95 out of 5 average rating, 422 reviews

The Log Cabin

A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Sep 21 – 28

G$22,030 GYD per night

Guest favorite

Cottage in Martinsburg

4.98 out of 5 average rating, 354 reviews

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

Oct 10 – 17

G$23,487 GYD per night