Holiday houses in Delaplane

Mountaintop Retreat with Wood Fired Hot Tub

Named Virginia’s most wishlisted Airbnb, Doah House is an architect-designed retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. Featured in Dwell and Travel + Leisure, the cabin is a container for rest and observation. The stay is shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing light, air, and sound. Each day feels different. The forest changes, and you might, too.

Seaton Place House

Located on the 60 acre Seaton Place Farm, circa 1840, this 2019 renovated 3 bedroom and 2 bath cottage is one of a kind. Sophisticated, but cozy. Charming, but informal. It is for those who are captivated by nature yet close to hunt and horse country, vineyards and the antique shops of Middleburg. The property boasts a stocked pond, abundant wildlife and three artificial golf greens for par 3 golf. Enjoy taking long walks down Carr Lane past the adjacent 2000 acres of protected pastureland.

"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!

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.

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.

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!

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.

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.

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 about 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 star gaze at night. Visit the local winery (5 mins. away) or hunker down to relax. Top-Rated Guest discount given!

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.

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!

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!