Vacation rentals in Middleway

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Top-rated vacation rentals in Middleway

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Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 567 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Sep 3 – 10

G$17,580 GYD per night

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 27 – Sep 3

G$25,748 GYD per night

Guest favorite

Treehouse in Shepherdstown

4.97 out of 5 average rating, 248 reviews

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Oct 8 – 15

G$32,085 GYD per night

Guest favorite

Home in Inwood

4.89 out of 5 average rating, 549 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 26 – Feb 2

G$17,844 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.

Jan 20 – 27

G$25,597 GYD per night

Guest favorite

Farm stay in Harpers Ferry

5.0 out of 5 average rating, 224 reviews

The Lodge Room at Mt. Mama Meadows Homestead

This listing is adults only. Mt. Mama Meadows Homestead is our own slice of “almost Heaven”. We're located in Harpers Ferry, a small historic town in Jefferson County, West Virginia, in the lower Shenandoah Valley. Whether you are coming to check out the surrounding Blue Ridge Mountains, hike the Appalachian Trail, raft the Potomac or Shenandoah rivers, delve into the rich Civil War history of the area, or just relax on the homestead, there is no shortage of things to do.

Jul 13 – 20

G$30,553 GYD per night

Guest favorite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 509 reviews

Beautiful suite, spa bathroom & gardens

Private-entry luxurious suite combining comfort & style for a memorable stay. Located in quiet neighborhood -- Harpers Ferry historic district -- 1920s stone foursquare home with beautiful gardens to explore. Close to National Park, Potomac & Shenandoah Rivers, C&O Canal Trail, AT, Amtrak train station, Storer College, & Loudoun Co. wineries. An ideal accommodation for a romantic couple's getaway. More pics on Insta @rockhavenbnb

Dec 1 – 8

G$30,278 GYD per night

Guest favorite

Cottage in Shepherdstown

4.96 out of 5 average rating, 181 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!

Feb 24 – Mar 3

G$25,236 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.

Jan 11 – 18

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 11 – 18

G$23,273 GYD per night