Holiday houses in Kernstown

4.99 out of 5 average rating, 404 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...

Superhost

Apartment in Winchester

4.82 out of 5 average rating, 128 reviews

The Comfortable In-Towner

A cute one bedroom apartment located on lower level of a historic 1840s home. This half basement has windows to let in natural light, a full-size kitchen with dishwasher, fridge, big closets, Queen size Tuft & Needle premium mattress and a private screened patio open to our courtyard with friendly neighbors and management on site. Window ac units, fans & radiators Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, shops cafes & entertainment.

4.97 out of 5 average rating, 142 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, 194 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, 207 reviews

Apartment 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, 281 reviews

Apartment 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.

4.97 out of 5 average rating, 198 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!

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!

4.95 out of 5 average rating, 188 reviews

Indigo Blue modern open vibe on tree lined street

Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style and relaxing outdoor areas! This 3BR 2BA home w/ sunroom w/ gas fireplace & rear fully fenced courtyard is the perfect place get away to & explore downtown Winchester. Walking distance to everything. Park & walk & enjoy nearby John Handley HS /walking mall /shopping/live music /art galleries/ walk to the iconic Handley Library, You will LOVE it!

4.95 out of 5 average rating, 211 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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Kernstown holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Kernstown

4.99 out of 5 average rating, 77 reviews

Farm stay in Strasburg

Homestead with Shenandoah Valley Views

AidanRating, 5 stars1 week ago

We loved our stay at Jenny’s place! The views were great, the place was spotless, and she even left us a half dozen farm fresh eggs for breakfast, which were delicious. They have a few cats that run around a lot upstairs, but they were not a problem (we saw a few in the window and they were adorable). We will want to come back out to the Shenandoah Valley again, and when we do, we really hope to stay here again!

4.75 out of 5 average rating, 4 reviews

Apartment/Great Private floor

ElliotRating, 5 stars3 weeks ago

Great place. We really enjoyed it. Plenty of space, clean, and functional. The hosts communicated well and weren’t overbearing at all. Great location in Winchester, street is quiet and a cool battlefield park in walking distance. We highly recommend!

Cabin in Berkeley Springs

5 out of 5 average rating, 52 reviews

Frog Hollow A Frame by Stay With Branch | Hot Tub

SaraRating, 5 stars1 week ago

Wonderful stay for our group of seven young women, with the perfect amenities and location for a relaxing and fun week away! The hosts were extremely responsive, friendly, and detailed with all their suggestions, help, and information! Loved the hot tub and fire pit in particular. Beautiful location and easy to get to town to explore. Thank you for a lovely stay, hopefully we’ll be back again!

5 out of 5 average rating, 15 reviews

Cottage in Front Royal

Riverfront Paradise | Hot Tub | Sauna | FirePit

ElinorRating, 5 stars1 week ago

Definitely coming back when the weather is warmer. TY Viktar for an amazing and peaceful weekend! Sauna and hot tub were amazing

5 out of 5 average rating, 6 reviews

Cabin in Front Royal

New! Zen Cabin in the Clouds

JohnRating, 5 stars1 week ago

We thoroughly enjoyed our stay! The cabin was in a peaceful location and was so relaxing. Natasha was the perfect host and made us feel special on our anniversary. The cabin was inviting, comfortable, and beautiful inside. The hot tub and porch were awesome and surrounded by a relaxing wooded setting. Would definitely stay again!

5 out of 5 average rating, 6 reviews

Cabin in Luray

"The Turtle" Romantic Luxury Cabin in Shenandoah

CatherineRating, 5 stars1 week ago

I enjoyed my time at Morry’s place. He was very professional and answered any questions I had in a timely manner. His beautiful home was peaceful. It was just as described, and my dog enjoyed himself. I look forward to booking again in the future.

Chalet in Augusta

4.81 out of 5 average rating, 145 reviews

Mountaintop Views, Hot Tub, Deck, Fire Pit & WiFi

KristenRating, 5 stars1 week ago

I booked this cabin as a surprise trip for my boyfriend's birthday and it was the best decision I could have made! Tony's place was even better than described. It was such a peaceful, beautiful property with the most amazing views, especially at sunset. We have stayed at a lot of different cabins, but we both agreed that we want to come back and stay at this one again. It was perfect!