Vacation rentals in Delaplane

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Top-rated vacation rentals in Delaplane

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Guest favorite

A well-maintained cabin is set against a backdrop of colorful autumn foliage. A grassy area features four blue chairs arranged around a fire pit, providing a cozy gathering spot. The deck extends from the cabin, offering views of the surrounding nature.

Home in Linden

Spacious Mountain Cabin

Welcome to our spacious mountain cabin, nestled atop 5 acres just outside of Shenandoah. With its blend of natural beauty and convenient proximity to a variety of attractions, our cabin is a great choice for creating unforgettable memories with your friends and family. We love waking to a symphony of birds attracted to the flowering shrubs & flowers and nodding off to the soothing lullaby of forest insects. Fireflies provide a beautiful display in the summer. The hot tub has great sunset views.

4.92 out of 5 average rating, 109 reviews

Top guest favorite

A porch view captures rolling hills and lush greenery, with fencing enclosing a vast open space. A small table is set for two, featuring glasses filled with a beverage and a propane firepit nearby, inviting relaxation amidst nature.

Guest suite in Markham

"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!

5.0 out of 5 average rating, 133 reviews

Guest favorite

A serene outdoor space is highlighted by a fire pit surrounded by custom-built Adirondack chairs. The spacious house is visible in the background, softly illuminated against a vibrant sunset. Lush green lawn and trees frame the scene, enhancing a peaceful atmosphere.

Home in Delaplane

ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room ★ Private Footpath to Winery

Featured in Washingtonian Magazine, Fox Chase is nestled on five acres in the heart of Virginia’s wine country and is connected by a private footpath to Blue Valley Winery. Perfect for large groups, it is an ideal base from which to explore the vineyards, horse farms, history, hiking, and cycling routes of the Piedmont. Just four miles from Marshall, eight miles from Paris and Upperville, and 13 miles from Middleburg, the house is also close to some of the region’s finest shopping and dining.

4.94 out of 5 average rating, 241 reviews

Top guest favorite

A covered outdoor patio is visible, featuring two wicker chairs with cushions and surrounded by planter boxes filled with flowers. A view of well-maintained greenery and a gravel area highlights the peaceful outdoor setting.

Cottage in Marshall

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. Please be mindful this property is near a train track, charming!

4.91 out of 5 average rating, 141 reviews

Guest favorite

A screened-in porch is shown with comfortable seating, including a pair of cushioned couches and a coffee table. A decorative sign reads 'Reserved for Mardi Gras Parade.' Natural light enters through large windows, and greenery is visible beyond the porch, enhancing the serene ambiance.

Cabin in Linden

Hidden Gem on Hidden Valley Lane

Full relax at this unique and tranquil getaway. Cute cabin in a park like setting with a wood burning fire place. A pond and lake view(mostly 3 seasons of the year). There is a hammock and a rope swing to enjoy. Trampoline for the kids. Starlink internet!!! Hike to a natural spring and a small creek that feeds Rappahanock river. Go fishing, hike the Appalachian trails near by or enjoy the list of local wineries. Front Royal is only 15 minutes away as well as Skyline Caverns and Skyline drive.

4.89 out of 5 average rating, 171 reviews

Guest favorite

Home in Delaplane

VA Wine Country Farmhouse w/ Private Winery Trail

Stay in a beautifully restored 1800s farmhouse in the heart of Northern Virginia wine and horse country—with a rare private trail directly to the neighboring winery. Perfect for vineyard tours, wine weekends, and guests attending nearby weddings, this spacious retreat offers 5 bedrooms, 3.5 bathrooms, and room for up to 14 guests. Enjoy peaceful countryside living just minutes from top wineries and wedding venues, with the unique ability to walk straight to wine tastings from your doorstep.

4.93 out of 5 average rating, 103 reviews

Top guest favorite

A glass of wine is positioned in the foreground, reflecting a sunset that casts warm hues across the sky. Lush greenery surrounds the scene, with the sun descending below the horizon, creating a serene atmosphere.

Home in Linden

Valley Vista, stunning views in wine country

Take advantage of low weekday rates and work from your country home with strong Wi-Fi! Sunsets and sensational views await you at this RUSTIC retreat set in the mountains, just a few miles from Shenandoah National Park and a little more than an hour from Washington, DC. Enjoy the wood burning stove in the winter and the mountain breezes in the summer. Sip wine from the hot tub and gaze down on the Shenandoah River valley below. Visit the local winery (5 mins. away) or hunker down to relax.

4.93 out of 5 average rating, 280 reviews

Top guest favorite

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

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!

4.99 out of 5 average rating, 163 reviews

Top guest favorite

Farm stay in Marshall

1910 Farmhouse on 6 Acres • VA Wine Country

Welcome to Badby Wood Farmhouse, a lovingly restored 1910 farmhouse on six private acres in Virginia’s horse and wine country. With 3 bedrooms, 2.5 baths, and room for up to 8 guests, it’s perfect for families, friends, and peaceful getaways. Explore nearby wineries, charming towns, and the Blue Ridge - or simply unwind in the countryside. Guests enjoy exclusive perks at nearby Barrel Oak Winery, including complimentary wine and special discounts. Proudly veteran owned and operated.

4.97 out of 5 average rating, 39 reviews

Top guest favorite

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

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.

4.98 out of 5 average rating, 206 reviews

Top guest favorite

A warm interior features a spacious bed dressed in a rich, burgundy coverlet, complemented by wooden wall panels and exposed beams. A cozy seating area is provided next to the bed, with light streaming in from a window adorned with wooden shutters.

Cabin in Delaplane

Herb Cottage-Elegant Cabin plus Optional Farm Tour

Our beautifully restored cabin is the perfect place to relax and enjoy the unique setting of our regenerative conservation farm and the local countryside and vineyards. This elegant cabin offers a charming kitchenette and accessible bathroom while retaining its pre-Civil War character with original wood floors and beams. Curl up in front of the wood stove or enjoy sundowners on the covered deck looking out on our lush pastures or next to the firepit and shared pool and hot tub.

5.0 out of 5 average rating, 156 reviews

Top guest favorite

Cabin in Linden

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!

4.97 out of 5 average rating, 142 reviews