Holiday rentals in Jordan Springs

4.9 out of 5 average rating, 354 reviews

Downtown 1920's Gas Station with Hot Tub

Luxury 1920’s Refurbished Gas Station and hot tub repurposed into a beautiful apartment. Private parking/EV charging station, private hot tub, full kitchen, custom rain shower, high speed wifi, and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, coffee nook, and an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

4.97 out of 5 average rating, 196 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

5 out of 5 average rating, 209 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, 282 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, 155 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.

Superhost

Loft in Winchester

4.72 out of 5 average rating, 658 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!

4.97 out of 5 average rating, 254 reviews

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Farm stay in Round Hill Village

4.93 out of 5 average rating, 412 reviews

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

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, 233 reviews

Full basement with private entrance. Hot tub

Cozy movie themed basement is exactly what you are looking for. Classic AirBnB-we are opening our house to you! Space is completely private. Bedroom with queen bed. High speed internet. Private bath w/shower. Small refrigerator, microwave, 2 flat screen TVs table and chairs and multiple couches in a large family room w/Sofa bed. 1000 square feet of space! Home 2 miles outside of the city of Winchester in Frederick County.

4.97 out of 5 average rating, 500 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.

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Other great holiday rentals in Jordan Springs

Guest house in Stephens City

5 out of 5 average rating, 17 reviews

Ventura Cottage: 360-views/HotTub/4 acres/Gym

JosetteRating, 5 stars2 months ago

Everything was top notch, pictures don't do the location justice. The ambiance is peaceful quiet fresh air beautiful views, the house is as listed and more, You get what you paid for. Leena is an amazing person very responsive and very hospitable. Don't think twice just book you will not be disappointed.

Barn in Berryville

4.78 out of 5 average rating, 120 reviews

Modern House Barn on 66 acre Horse Farm

LisaRating, 5 stars2 months ago

This place is tucked into a little peace of heaven. Very peaceful and easy to get to. The interior is nicely designed, furnishings are comfortable. The kitchen has a little eat in area with plenty of space to sit and chat, eat, play board games, or cook. I loved that the bedrooms were upstairs so if someone wanted to sleep, it’s quiet enough to do that. The upstairs is quite sound proof. There’s also a nice little tv area upstairs between the two rooms. The rooms have plenty of space to store clothes if you are staying longer. The outside area also has a picnic table and grill which would be nice when staying in the warmer months. The hosts were very kind and responsive. They answered any questions we had quickly. I highly recommend this place and hope to stay again when we come back.

4.95 out of 5 average rating, 77 reviews

Easy like a Sunday Morning 1 BR apt great location

VirginiaRating, 5 stars2 weeks ago

Kim's communication was good. The Place is in a very old building, but was fine for overnight.

Superhost

4.65 out of 5 average rating, 37 reviews

The Flat of Old Town Winchester

TheresaRating, 5 stars3 weeks 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.

4.95 out of 5 average rating, 41 reviews

Cabin in Historic Old Town Winchester

HersonRating, 5 stars1 week ago

Great location next to old town! Lots to do if you want to go out for a walk and many places to dine in. Felt like home and enjoyed the backyard area. Highly recommend!

5 out of 5 average rating, 27 reviews

Cabin in Culpeper

Campo Cibola - Brisa

MichelleRating, 5 stars4 days ago

It was so peaceful and beautiful. Loved the quiet !! Tried my first bison steak and I was surprised that I liked it . We enjoyed our short getaway .

4.99 out of 5 average rating, 79 reviews

Home in Berryville

Deer Chase

BonnieRating, 5 stars1 day ago

Jeanne was an outstanding host! Easy to communicate with quick responses to any questions. The house was amazing and truly exceeded our expectations. It was spotless! The cleanest rental I have ever stayed in. The grounds were so serene I didn’t want to leave. Thank you for making our weekend getaway such a success!