Holiday rentals in Ashby

4.98 out of 5 average rating, 255 reviews

Riverhouse, a HOT TUB Mid Century RIVER Escape!

~Break FREE and lift your soul at Riverhouse! Sleeps 5 and only a 60 min drive from Washington, DC and NOVA! Picture HOT TUB relaxation with FRONT ROW RIVER VIEWS, serene privacy, and an eclectic, unforgettable vintage vibes~ Whether relaxing on your private deck or in the NEW hot tub, let the river carry your worries away and the fresh air bring you back to life! To energize, decompress, release your inner creativity, or fall in love ~for the first time or over again, choose Riverhouse!

Guest suite in Front Royal

4.99 out of 5 average rating, 130 reviews

Chapel View Nest: Patio, Firepit and Views.

Stay in our secluded getaway on 20 acres with skyline mountain views and stunning sunsets. The main house is perched atop a hill with the English basement attached. Guests will have their own private sunny patio with a gas fire pit and grill. Relax and unwind in this welcoming tucked away spot that is private and tastefully furnished with everything you need for a wonderful stay. Nearby: Christendom College ~1 m Warren Memorial Hospital 2.5 m Shenandoah Park Skyline Dr. 6 m Front Royal 6 m

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

4.98 out of 5 average rating, 198 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.

4.99 out of 5 average rating, 119 reviews

Beautiful mountain cabin, lake, recreational areas

Blue Mountain Cabin is situated at 1,700 feet. Fish, swim, walk to nearby private Deer Lake. Located in Front Royal on Blue Mountain near Skyline Drive, Skyline Caverns, Wildlife Management Area, Appalachian Trail, G.W. National Forest, Fox Meadow Winery. Horseback riding nearby. Near the town of Front Royal, city of Winchester and outdoor movie theatre in Stephens City. Element on Main Street, Spelunker's and Melting Pot Pizza, local favorites. We offer wi-fi, landline phone, TV, views!

4.98 out of 5 average rating, 119 reviews

Flat in Front Royal

Cozy 1BR for Couples & Solo Travel~No Cleaning Fee

Welcome to Cozy Hideaway, your Shenandoah Valley retreat! Enjoy an upstairs space with a queen bed, full bath, washer/dryer, and mini kitchenette with microwave and fridge. Local art adds charm. With a private 2nd-floor entry, you’re near the Shenandoah River for fishing and kayaking, and 8 mins from Skyline Drive—perfect for nature lovers. Guests like Steve (Aug 2024) say: 'Fun, friendly, comfy, affordable—you do Airbnb right!' Note: Stairs required; we’ll help with bags if you’d like.

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!

4.94 out of 5 average rating, 214 reviews

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!

4.97 out of 5 average rating, 177 reviews

Cabin in Lost River

Rustic and stylish mountain getaway

The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

4.93 out of 5 average rating, 245 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.

Superhost

Guest house in Maurertown

4.85 out of 5 average rating, 257 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.

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Popular amenities for Ashby holiday rentals

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Other great holiday rentals in Ashby

5 out of 5 average rating, 25 reviews

Flat in Front Royal

NEW! Unit 12~Pet Friendly ~ Hiking

RachaelRating, 5 stars1 day ago

Great spot to be central to skyline drive. Bed was very comfortable

Superhost

4.92 out of 5 average rating, 49 reviews

Skyline Shenandoah! Hot Tub DogOK EV Charger Grill

KatherineRating, 5 stars3 days ago

quick note on the bathroom. The towel hanger is a bit wonky falls off the wall if the grab the towel the wrong way

4.96 out of 5 average rating, 23 reviews

Guest suite in Linden

Blue Ridge Mountain Retreat

Thomas "Randy"Rating, 5 stars2 weeks ago

The location was beautiful & quite. The lodging was clean and well laid out and comfortable. We were able to have a very relaxing time away.

5 out of 5 average rating, 43 reviews

Cabin in Swanton

Chalet in the Orchard; Romance, Luxury, Relaxation

AveryRating, 5 stars1 week ago

beautiful home — even more than the pictures portray. the best romantic getaway, the property is gorgeous inside and out. highly recommend!!

4.86 out of 5 average rating, 37 reviews

Flat in Winchester

Dreamweaver Bright 1BR 2 blocks to Walking Mall

EricRating, 5 stars5 months ago

Great place with a lot of character and nice touches. Wonderful location. Would definetly stay again!

4.94 out of 5 average rating, 81 reviews

Home in Front Royal

Entire house up to 6 and 2 pets allowed

VictoriaRating, 5 stars1 week ago

Athena was super friendly and helpful throughout my stay. The house was just as described—clean, comfortable, and fairly priced. What you see is what you get, and it met my expectations perfectly. She was also very accommodating of my 85-pound fur baby which made the stay even more enjoyable. Would definitely stay again!

4.98 out of 5 average rating, 59 reviews

Cabin in Linden

The Grape Escape - A-Frame Cabin in Wine Country

BrynRating, 5 stars1 week ago

Jackie’s place was just like a little piece of heaven and tranquility with all the little perks! From comfortable and clean blankets, to a fire ring and swing, and cute phrased signs and such throughout the cabin. We only stayed 1 night but could see spending a long weekend and exploring the local wineries and another visit to Shenandoah Park (the reason we picked her place)! This little A-frame opens up to an updated space with a rustic feel… a must visit! The Grape Escape is off the beaten path and if you need a relaxing recharge this is the place to stay!!