Holiday rentals in Opequon

4.99 out of 5 average rating, 406 reviews

Cottage in Winchester

Uber SXY Private Country Escape! Hot Tub & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

4.97 out of 5 average rating, 143 reviews

Cabin in High View

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

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 !

4.98 out of 5 average rating, 197 reviews

Campsite in Front Royal

Blue Mountain Hideaway • Enchanting Glamping Stay

Unplug and unwind at Blue Mountain Hideaway, a boutique glamping tent nestled in the woods near Shenandoah National Park and the Shenandoah River. Enjoy a real bed, a fully equipped outdoor kitchen, and complimentary firewood—no WiFi, no distractions, just the sounds of nature. Cozy up by the fire, savor slow mornings, and reconnect with what matters most. Just bring your cooler and clothes—we’ll handle the rest. Perfect for couples, solo travelers, and anyone craving a quiet place to reset.

5 out of 5 average rating, 209 reviews

Flat in Winchester

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

Flat in Winchester

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.

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.

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.

4.96 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 Opequon

5 out of 5 average rating, 31 reviews

Cabin in Luray

Horizon | Hot/Cold Tub, Fireplaces, Sauna, EV Plug

KateRating, 5 stars3 days ago

What a beautiful place. We felt right at home, and spend several hours just decompressing on the spacious deck with a spectacular view. Watched storms drift across the valley, and bird of prey swoop across the skies. Sounds of nature everywhere, and all the comforts of home inside. The interior is thoughtfully appointed, and has just enough without over doing the comfortably compact space. The car charger was also extremely appreciated. Many choices of easy daily adventures, too. We enjoyed Luray, Sperryville and DuCard Vineyards. Thank you Skyline Properties for a wonderful stay.

4.99 out of 5 average rating, 78 reviews

Farm stay in Strasburg

Homestead with Shenandoah Valley Views

LaurenRating, 5 stars2 weeks ago

What a great stay in a peaceful quiet setting! Thanks Jenny!

4.95 out of 5 average rating, 77 reviews

Flat in Winchester

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.

5 out of 5 average rating, 10 reviews

Cabin in Luray

"The Turtle" Romantic Luxury Cabin in Shenandoah

JenniferRating, 5 stars1 day ago

Morry has been an excellent host and responsive with any questions we had! The cabin's location is so convenient! About 10 minutes drive to the nearest major retail grocery store / fast food chains and 15 minute drive into Luray's city center for additional options on cafes and restaurants. Nearest Shenandoah Entrance will be Thornton Gap Entrance (24 minutes). With everything in a reasonable vicinity, makes planning so much easier and allowed us more time to spend on trails/relaxing. The cabin itself is gorgeous and well equipped with needed amenities! The hot tub was a big hit after coming back from hiking and a great way to end the day with a good soak. Appreciate Morry for allowing us to stay at this beautiful cabin and can't wait to be back!

4.95 out of 5 average rating, 59 reviews

Misty Meadow has quite setting in the country.

KerinaRating, 5 stars3 days ago

This is the second time staying in this beautiful home. Marie has everything you need for a perfect stay. The area is so beautiful and the home is soooo cozy. We will definitely be back.

4.99 out of 5 average rating, 81 reviews

Apartment in Winchester

Historic District Downtown Winchester

PattyRating, 5 stars1 week ago

Great spot and beautifully decorated. Close to lots of eating places.

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!