Holiday rentals in Stephens City

4.93 out of 5 average rating, 107 reviews

Home in Middletown

Cozy Reliance Retreat with Beautiful Views

Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps four and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

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, 208 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.

4.73 out of 5 average rating, 657 reviews

Loft in Winchester

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.

4.94 out of 5 average rating, 214 reviews

Cabin in Front Royal

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

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.

Guest house in Maurertown

4.85 out of 5 average rating, 256 reviews

Studio along i81: Near Wine, Beer, Hiking & Nature

Newly renovated detached studio guest-suite located in the beautiful Shenandoah County with country feels and easy access to I81. It features a butcher block bar for eating/working, a queen size bed, tv with Netflix along with Chromecast so you can cast your favorite shows from your phone/laptop, and during the summer you'll have the quietest and smart ac unit on the market. It has a shared driveway with the host's primary residence.

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.

4.96 out of 5 average rating, 129 reviews

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!

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Other great holiday rentals in Stephens City

Private room in Winchester

4.98 out of 5 average rating, 113 reviews

Winchester Private Room

BenjaminRating, 5 stars5 days ago

Holly’s place was cozy, clean, and comfortable. Excellent place to spend the night during a long road trip.

5 out of 5 average rating, 9 reviews

Lovely 1100 Sq. ft. 1 bedroom basement apartment

LeeRating, 5 stars1 week ago

We enjoyed staying at Martin’s home.The house was well stocked, clean and there was even a basket of welcome snacks. 😊 The yard was beautiful with gardens and there were birds all the time right out by the kitchen window. Our daughter lives in the area and we enjoyed it so much we have it booked for 2 more visits.

4.95 out of 5 average rating, 77 reviews

Easy like a Sunday Morning 1 BR apt great location

VirginiaRating, 5 stars1 week ago

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

5 out of 5 average rating, 3 reviews

Home in Harpers Ferry

Gorgeous cabin on Blue Ridge

JamieRating, 5 stars6 days ago

We had a wonderful weekend in this sweet cabin! From before check in, until check out Flora made the whole experience easy and comfortable. There are so many thoughtful details throughout this property. Super clean and beautiful inside, but we spent most of our time enjoying the incredible deck. Our favorite part was that we could still sit outside in comfy seats and watch a thunderstorm while covered! Close to lots, but far from it all. We can’t wait to come back!

5 out of 5 average rating, 33 reviews

Whole 3-bedroom house walkable to downtown.

GiniRating, 5 stars2 months ago

We thoroughly enjoyed our extended stay in this charming cottage! The location is ideal for walking—- either around the neighborhood or downtown. We loved the charm and cozy atmosphere and spent a lot of time on the sun porch too! Can’t recommend it highly enough and look forward to staying here again

4.69 out of 5 average rating, 36 reviews

The Flat of Old Town Winchester

TheresaRating, 5 stars2 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.

4.9 out of 5 average rating, 10 reviews

Skyview Farmhouse

SaraRating, 5 stars6 days ago

We had a wonderful stay at Denise’s farmhouse with our family. Her house is beautiful, very clean, and extremely comfortable and inviting. She has thought of every detail and includes extra amenities like snacks, toiletries, board games, and plenty of linens. We had our young son with us, and she laid out many things for him like a portable crib, baby shampoo and towels, a bathtub, and a changing pad. The location is beautiful and not far from restaurants, shops, etc. All the beds and furniture were very comfortable, and there was plenty of space for everyone. As a host, Denise was extremely responsive and made things very easy for us. I would recommend her house to anyone!