Holiday rentals in Delaplane

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Top-rated holiday rentals in Delaplane

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.
Cottage in Winchester
4.99 out of 5 average rating, 471 reviews

COZY+SEXY 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...

Guest favourite
A spacious deck offers unobstructed views of rolling hills and valleys, accented by vibrant autumn foliage. The sky is expansive, displaying soft clouds and blue tones. A sleek railing encircles the deck, enhancing the serenity of the natural landscape.
Cottage in Markham
4.94 out of 5 average rating, 186 reviews

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Top guest favourite
Flat in The Plains
4.98 out of 5 average rating, 689 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, wi-fi, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Top guest favourite
A winding path is bordered by vibrant flowers and lush greenery, leading to an expansive view of the Shenandoah Valley. The sky overhead is filled with fluffy clouds, framing the distant mountains that rise majestically in the background.
Guest suite in Markham
5 out of 5 average rating, 127 reviews

"The Love Nest" - Stunning Views in Wine Country!

The Love Nest overlooks the Shenandoah Valley and perches high on a mountain with thousands of acres on all sides including the Thompsons Wildlife Reserve & Appalachian Trail. Wake up watching a beautiful sunrise while sipping coffee from your porch with glorious mountain views. The Love Nest is a great place to rest, relax, & recharge in a quiet, tranquil setting. Located just three miles off Rt. 66, it is centrally located near wineries, hiking, sightseeing, events, restaurants, and more

Top guest favourite
A wooden staircase leads to the cabin entrance, framed by lush greenery. Railings provide support along the steps, which are surrounded by natural landscaping. A covered porch can be seen in the background, inviting guests to explore the welcoming outdoor area.
Cabin in Front Royal
4.99 out of 5 average rating, 156 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!

Top guest favourite
A bay window offers a panoramic view of the lush greenery and rolling hills beyond. Two comfortable chairs are set on a deck, inviting relaxation with a scenic backdrop of mountains under a clear sky.
Home in Markham
4.98 out of 5 average rating, 204 reviews

Virginia Wine Country Retreat 60 mi. from DC

Quiet and serene, this Wine Country Retreat in Fauquier County is an easy 60 mile drive from DC. Enjoy privacy and natural beauty in a 4-BR, 6,000 SF home on 11+ acres, with gorgeous views of the foothills of the Blue Ridge Mountains. Lovely antiques and modern amenities, WiFi, washer/dryer, gourmet kitchen. 1st floor BR, 3 more upstairs. Large deck for cookouts or stargazing! Perfect for groups doing winery tours, a "girls get-away" weekend, family gatherings, corporate retreats.

Top guest favourite
A classic A-frame cabin is surrounded by trees, featuring a spacious deck with comfortable lounge seating. Soft lighting accentuates the inviting outdoor space, while large glass doors provide a glimpse into the cozy interior. The modern roof complements the rustic wooden facade.
Cabin in Front Royal
4.96 out of 5 average rating, 294 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!

Guest favourite
Cabin in Linden
4.97 out of 5 average rating, 135 reviews

Wilderness Ridge | Private Cabin w/ Mountain Views

"Wilderness Ridge" is the perfect private refuge to soak in the stunning views of the Shenandoah Valley while spending time with friends and family. The cabin features a full kitchen, theater room, and propane fireplace. The home’s location lets you tour local vineyards less than five miles away, or visit the famous Apple House for apple cider donuts. As night falls, return home for a BBQ on the deck while the sun sets over the valley and mountains below!

Top guest favourite
A modern cabin is set amongst lush greenery, featuring a dark exterior and a welcoming front porch. Surrounding landscaping includes a variety of shrubs and trees, creating a peaceful atmosphere. The driveway leads to the entrance, providing easy access to the secluded retreat.
Cabin in Star Tannery
4.96 out of 5 average rating, 277 reviews

Cabin With Wood Burning Hot Tub

Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

Guest favourite
A wooden walking bridge connects to a secluded cabin situated on an island, surrounded by lush greenery and a calm lake. Gentle hills rise in the background, providing a scenic view of the countryside.
Cabin in Upperville
4.94 out of 5 average rating, 173 reviews

Island cabin

Getaway from the city and escape to the countryside in this beautiful cabin recently renovated. Situated on a beautiful private lake, enjoy your morning coffee on the porch over looking the water, or enjoy the fire pit with the sunset. The cabin features a queen size bed, a full bathroom, a kitchenette, and a cozy living room area. There is also an outside grill and fire pit. We recently updated the kitchen and added a full size fridge/freezer.

Guest favourite
A modern cabin is nestled among trees, featuring a sleek design with large windows that allow light to emanate from within. The surrounding rocky terrain is softly illuminated by exterior lighting, creating a calm ambiance in the early evening fog.
Cabin in Front Royal
4.99 out of 5 average rating, 426 reviews

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.

Top guest favourite
A spacious living area features a light-colored sofa positioned on a patterned area rug. Exposed wooden beams grace the ceiling, enhancing the rustic charm. A stone fireplace provides a focal point, while natural light enters through large windows, illuminating the warm interior.
Cabin in Linden
4.97 out of 5 average rating, 237 reviews

Cedarbank • Cabin in Virginia Wine Country

Come visit Virginia wine country and nearby Shenandoah National Park in this modern log cabin. The Cedarbank cabin carries all the conveniences of modern living including updated kitchen and WiFi. Though the grounds are only an hour from Washington DC, Cedarbank feels like a world apart, providing relaxing views and 7 tranquil acres for the perfect rejuvenating country escape. SEE NOTES ABOUT OUR AMENITIES

Popular amenities for Delaplane holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Fauquier County
  5. Delaplane