Holiday rentals in Ashby

4.98 out of 5 average rating, 254 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, 128 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

4.99 out of 5 average rating, 246 reviews

Valley View Cabin

The coziest little cabin to getaway from the hustle and bustle of the city, but only an hour away from Washington DC. Our hope is you enjoy every part of your stay at this little cabin; from enjoying your morning cup of coffee on the screened in porch while watching deer or turkey graze in the yard, or venturing to the quaint Main Street of Front Royal. This town has so much to offer. Only 15 minutes away from Shenandoah National Forest & skyline drive. A perfect place for kayaking & canoeing!

4.93 out of 5 average rating, 106 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, 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.

4.99 out of 5 average rating, 117 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, 118 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.

4.97 out of 5 average rating, 199 reviews

Home in Winchester

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!

5 out of 5 average rating, 232 reviews

Holiday home in Linden

Hottub+Pet friendly+Mtn view+Skyline Dr+Wineries

Cozy mountain cabin with a hot tub, fire pit, and picnic/grilling area that you can enjoy as you gaze out at the mountains or stars! Something you don’t find every day. Sip your morning coffee on the deck, play one of the many board games, read a book from our library, play a retro arcade game, or just enjoy nature. The cabin is close to a lot of wineries, hikes (Appalachian Trailhead is just a few minutes away), Skyline Drive, Front Royal downtown, Caverns, and many more attractions.

4.97 out of 5 average rating, 141 reviews

Yurt in Front Royal

Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Skyline Yurt is a one-of-a-kind luxury getaway nestled in the tranquil serenity of the mountains. Here, you won't find any compromises with respect to the top-notch cabin-like structure, modern amenities, a hot tub, wood-burning stove, archery, EV charger, spacious elevated deck, pool table, board games, and so much more! This magnificent pet-friendly Skyline Cabin / Yurt is surrounded by the captivating scenery of Virginia's Blue Ridge Mountains at an elevation of over 1,100 ft!

4.95 out of 5 average rating, 211 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!

4.93 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.

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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, 23 reviews

Flat in Front Royal

NEW! Unit 12~Pet Friendly ~ Hiking

AmandaRating, 5 stars1 week ago

Awesome little place! Highly recommend. Lots of walkable restaurants and ubers available to wineries!

Superhost

Cabin in Linden

4.91 out of 5 average rating, 75 reviews

*NEW* Black Luxe A-Frame w/ Spa, Gameroom, Movie

DavidRating, 5 stars1 month ago

Had a peaceful, relaxing weekend with the family at the cabin! Everyone loved the hot tub and the kids settled right in with the projector / game room. Leah was super responsive and helpful with our questions.

4.96 out of 5 average rating, 23 reviews

Guest suite in Linden

Blue Ridge Mountain Retreat

Thomas "Randy"Rating, 5 stars1 week 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.

4.95 out of 5 average rating, 76 reviews

Campsite in Flint Hill

Vineyard Camping

OliviaRating, 5 stars1 month ago

This is a beautiful camping spot. It was very secluded and peaceful with views of the vineyard. There is a good fire pit, chairs, logs, trees great for a hammock, and everything you’d want in a campsite. Be sure to ask for the video guide to the campsite early. We camped in the wrong spot on the first night, but once we got the video it was much more straightforward. The bathrooms were cleaned very well, although as this is a rural area they did have a stink bug/wasp problem. Comes with the territory. Overall a great stay.

4.98 out of 5 average rating, 66 reviews

Home in Front Royal

The Forest Glade House

BillyRating, 5 stars1 month ago

This house was beautiful! We gathered for a friends reunion and had a great time. The house was spacious, and everyone felt like we had a great bedroom to retreat to. The kitchen was fully stocked, and the views were pretty. We had a small issue and the owners were on site right away to resolve it. We’d definitely go back!

4.98 out of 5 average rating, 58 reviews

Cabin in Linden

The Grape Escape - A-Frame Cabin in Wine Country

BrynRating, 5 stars5 days 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!!

4.99 out of 5 average rating, 78 reviews

Apartment in Winchester

Historic District Downtown Winchester

KelvinRating, 5 stars1 month ago

Alison's place is great if you value being walkable to Old Town. We prefer this over staying at the Wyndham Grand because of the separate room for our baby to sleep in. The kitchen is modern and fridge with a water filter is clutch. We didn't try to make any meals. Bed was clean/firm, HVAC was responsive, and lounge chair in the sitting area was comfortable. You can hear the train and street noise (especially cars w/o mufflers) at night, but I assume that's the case if you stay anywhere near Old Town.