Vacation rentals in Millwood

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Top-rated vacation rentals in Millwood

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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!

Oct 3 – 10

R2,410 ZAR per night

Guest favorite

Home in Bluemont

4.87 out of 5 average rating, 206 reviews

The Old Schoolhouse at High Meadows Estate

The Old Schoolhouse at High Meadows is a beautifully appointed historic cottage set amidst a tranquil 50 acre estate of gardens and old barns. Close to wineries, breweries, the Appalachian and W&OD Trails and many historic villages (Middleburg, Upperville, Harpers Ferry) and only minutes from the Shenandoah River, this superbly decorated cottage is a wonderful get away from Washington DC and perfect for a couple or small family. Activities abound, or just visit local farmers’ markets and read.

Aug 5 – 12

R2,874 ZAR 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.

Sep 4 – 11

R2,351 ZAR 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

R2,890 ZAR 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!

Apr 12 – 19

R2,887 ZAR per night

Guest favorite

Apartment in The Plains

4.98 out of 5 average rating, 447 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Jun 23 – 30

R1,681 ZAR per night

Guest favorite

Campsite in Front Royal

4.99 out of 5 average rating, 106 reviews

Blue Mountain Hideaway Boutique Camping Experience

Escape to a truly unique camping experience at our creek-side retreat. This park-like paradise is perfect for hassle free camping, all you need to bring your cooler and clothes. We provide everything else! Take advantage of heavily discounted off season rates! Throughout the winter season we will be opening our calendar two weeks in advance, weather dependent to ensure that our off grid water does not freeze. A propane heater is provided to ensure your sleep space is warm and toasty.

Mar 28 – Apr 4

R3,003 ZAR 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.

Apr 11 – 18

R2,337 ZAR 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.

Aug 6 – 13

R1,844 ZAR per night

Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 289 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.

Dec 4 – 11

R2,099 ZAR per night

Guest favorite

Home in Berryville

4.95 out of 5 average rating, 190 reviews

Riverfront Getaway w/ Breathtaking Views!

Welcome to the Shenandoah Valley! Expect a private, serene, and relaxing experience! Our newly renovated home has great deck space and beautiful views right on the Shenandoah River! Enjoy river tubing, fishing, kayaking, reading a book by the fire, or drinking coffee on the porch while watching a breathtaking sunrise! Conveniently located an hour west of DC and 25 minutes east of Winchester.

Jul 18 – 25

R6,804 ZAR per night

Guest favorite

Tiny home in Linville

4.99 out of 5 average rating, 602 reviews

The spring house at Thistle Hollow

Beautifully renovated spring house on the grounds of the 1800s Peter Breneman House. Soak up peace and quiet in one of the most beautiful corners of the Shenandoah Valley. Enjoy starry skies, sunrises, and birdwatching from your private porch. 9 minutes from Eastern Mennonite University, 13 minutes from James Madison University, and 45 minutes from the entrance to Shenandoah National Park.

Aug 10 – 17

R2,143 ZAR per night