Vacation rentals in Delaplane

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.

Location · Family · Hiking

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!

Family · Value · Quiet

"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!

Location · Value · Hiking

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.

Value · Location · Pets

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!

Location · Family · Getting around

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.

Value · Location · Kitchen

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.

Family · Location · Check-in

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.

Value · Family · Quiet

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.

Family · Location · Pool

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!

Value · Location · Getting around

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!

Family · Value · Parks

Cobbler Mountain Revival | Historic Farmhouse+View

Step into history at Cobbler Mountain Revival—a restored 1904 farmhouse at the base of Cobbler Mountain in Virginia wine country. This unique home is filled with antiques, historical figurines, and curated relics. Perfect for history lovers, hikers, and serenity seekers, it offers mountain views, trail access, and is steps from Cobbler Mountain Cellars Cidery. Enjoy modern amenities wrapped in the charm of early 20th-century craftsmanship.

Location · Family · Sleep quality