Holiday rentals in Stephenson

4.95 out of 5 average rating, 153 reviews

Home in Inwood

Lindas Country Cottage

Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

5 out of 5 average rating, 207 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.

4.97 out of 5 average rating, 281 reviews

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

4.99 out of 5 average rating, 152 reviews

Cabin in Gerrardstown

The Nest: Cozy Chalet w/Wi-Fi, Deck & Grill

The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the countryside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

4.97 out of 5 average rating, 198 reviews

Home in Winchester

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!

Superhost

Loft in Winchester

4.73 out of 5 average rating, 656 reviews

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

Tiny home in Harpers Ferry

4.98 out of 5 average rating, 120 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. The property features a large patio, outdoor dining area, courtyard, firepit, hammock, hot tub. The outdoor space provides private vistas of the Shenandoah, moonlit nights, star gazing while soaking in the hot tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Guest suite in Winchester

4.81 out of 5 average rating, 339 reviews

Safe, cozy oasis with private living & bath.

Wonderfully comfortable basement apartment. We are less than a mile from Winchester Medical Center.... ideal for traveling doctors/nurses. Close to other area attractions. You will have your own living room, bathroom and bedroom. Private entrance. Digital lock. You will get instructions prior to check in. You will be in the basement however it has natural light in the bedroom. There may be some noise from upstairs, but it is generally quiet.

4.93 out of 5 average rating, 243 reviews

Townhouse in Winchester

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.

4.97 out of 5 average rating, 497 reviews

Cottage in Winchester

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

4.91 out of 5 average rating, 103 reviews

Newly repurposed Historic Home in Winchester VA!

The historic “Homespun” is located on the border between Frederick County and the city of Winchester. Originally built in the mid 1790’s the Homespun is significant in local architecture as an example of a dogtrot-plan structure, a rare building form of this period. The property is listed on the National register of Historic Places and Virginia Landmark Registry.

4.98 out of 5 average rating, 420 reviews

Cottage in Martinsburg

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.

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Other great holiday rentals in Stephenson

5 out of 5 average rating, 9 reviews

Home in Charles Town

Harper Ferry

RoseMariaRating, 5 stars5 days ago

Sui’s home was very clean, spacious and comfortable. Sui was very responsive and a great host!

Cabin in Berkeley Springs

5 out of 5 average rating, 8 reviews

Rocky Ridge

LynnRating, 5 stars1 week ago

It is an interesting and absolutely beautiful drive to get to Geoff and Sharyn’s cabin from Berkley Springs. Once there, access is easy and the place is cozy, comfortable and really nice and cutely furnished. The view from the porch was my favorite part-absolutely stunning!! And if you happen to be there during a thunderstorm, that’s pretty amazing too! Lol Last (but not least), Geoff and Sharyn are excellent hosts. They promptly responded whenever I messaged them and their thoughtfulness is evident in so many ways. I would definitely stay here again!

4.99 out of 5 average rating, 78 reviews

Apartment in Winchester

Historic District Downtown Winchester

KelvinRating, 5 stars1 month ago

Alison's place is great if you value being walkable to Old Town. We prefer this over staying at the Wyndham Grand because of the separate room for our baby to sleep in. The kitchen is modern and fridge with a water filter is clutch. We didn't try to make any meals. Bed was clean/firm, HVAC was responsive, and lounge chair in the sitting area was comfortable. You can hear the train and street noise (especially cars w/o mufflers) at night, but I assume that's the case if you stay anywhere near Old Town.

Superhost

4.69 out of 5 average rating, 35 reviews

The Flat of Old Town Winchester

TheresaRating, 5 stars1 week ago

The room was just as pictured and described. It was easy to find. The directions were clear. The room had a guest binder that made it easy to find a restaurant and I even enjoyed reading through the town history book. When we drove around town I pointed out buildings I had just learned about! There are motion activated lights in the hallways that I thought were a great touch! I loved the designated parking in the back.

5 out of 5 average rating, 17 reviews

Home in Kearneysville

WV Cozy Cabin Summit Point Races

DeniseRating, 5 stars5 days ago

The Cozy Cabin was the absolute best stay we've had in this area so far. The Farm was absolutely gorgeous and peaceful, well cared for, very spacious and plenty of room for my dog to romp around. The charm of the Cozy Cabin was on another level. Beautiful soft color. An open air feeling and the beds were so comfortable, you melted into them. Everyone said it was the best sleep they had away from home. The Hosts were so friendly and responsive, we absolutely love them and loved our stay. Please look no further when considering a place to stay.

4.95 out of 5 average rating, 39 reviews

Home in Winchester

Cabin in Historic Old Town Winchester

StephanieRating, 5 stars2 weeks ago

We loved the character and unique flow of the house. It had everything we needed and was very clean and well put together. The whole neighborhood has a lot of charm and it is an easy and quick walk to the downtown shops and restaurants. We would definitely stay here again!

4.94 out of 5 average rating, 83 reviews

Cabin in Winchester

Foxtrot Mokki | Springtime Getaway 2 Hours from DC

RachelRating, 5 stars5 days ago

Our stay at Foxtrot Mokki was magical! Besides the sheer beauty of the property, the experience was seamless and made our vacation very relaxing. Definitely recommend exploring the amazing literature in the main bedroom! We enjoyed the luxurious, yet comfortable vibe of the home and would happily book again! Thank you to Tom & Geoff for being such wonderful hosts and for creating such a memorable experience for us.