Holiday rentals in Delaplane

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!

Secluded Farm Cottage | 265 Acres of Peace &Nature

Feel your body & mind relax and unwind as you take in this beautiful mountain home. A restful retreat for the old soul. Please see photos for important information regarding historical artifacts in the cottage. If you want to unplug, unwind, and find peace, all within a 10 minute drive to town, this is your place. Pastoral, quaint, and located on an historical farm dating back nearly 200 years. Get in touch with nature and find yourself. Our cottage is meant to evoke memories and warmth.

Charming 3BR Farmhouse • Wine Country Getaway

Welcome to Badby Wood Farmhouse, a charming retreat nestled in the heart of Fauquier County. Inspired by the timeless charm of an English village, this lovingly restored 1915 gem sits on six peaceful acres of open pasture and tranquil woodland—ideal for quiet getaways, family retreats, or a romantic weekend. With 3 inviting bedrooms and 2.5 bathrooms, the property sleeps 8 comfortably. Badby Wood offers a warm, welcoming escape in the heart of rural America. Proudly veteran owned and operated.

"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!

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!

Wine Country, Hikes & Dogs!

The Trails Home Farm is a unique dog and family-friendly country home with modern amenities. Over a dozen nearby wineries and hikes. Delicious restaurants. Located on 52 bucolic acres. This home is part of Homeward Trails Animal Rescue with rescued dogs housed separately on site for visiting (or not). Every visit supports the rescue of homeless animals. Starry night skies. Fireplace, firepit, deck, porch, sleeps up to 9 people. Super dog friendly. Great getaway for friends & family alike.

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.

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!

The Lodge at Turkey Creek

Your low-tech getaway awaits in the heart of the coveted Virginia Piedmont horse & wine country! Nestled in the woods at the end of a half mile private drive you will find quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, quaint towns, idyllic scenery, mountains and wineries. Only 40 min to Shenandoah Nat’l Park & 20 min to Sky Meadows State Park.

Atoka Cottage

This charming 3 bedroom/2 full bath home is fully equipped with everything you could need for a relaxing getaway in the Virginia countryside. Conveniently situated on scenic Atoka Road, this cottage is less than a 10 minute drive from the shops, restaurants, and wineries of Middleburg & Marshall. Highlights include a spacious master suite, and a cozy living room with an adjoining deck overlooking the peaceful backyard.

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.