Vacation rentals in Delaplane

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Delaplane

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

0 of 0 items showing

1 of 3 pages

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

5 out of 5 average rating, 108 reviews

The Love Nest

The Love Nest overlooks the Shenandoah Valley and perches on 12 acres surrounded by 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, and recharge in a quiet, tranquil setting. Located just 3 miles off Rt. 66, it is centrally located near wineries, hiking, sightseeing, events, restaurants, and more!

Superhost

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

4.89 out of 5 average rating, 110 reviews

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!

Top guest favorite

A spacious bell tent is positioned on a wooden deck, surrounded by natural stone and lush greenery. Soft lighting is visible inside, enhancing the inviting atmosphere. Sturdy steps lead up to the tent entrance, framed by earthy tones and the sounds of nature.

Campsite in Front Royal

4.99 out of 5 average rating, 216 reviews

Blue Mountain Hideaway • Enchanting Glamping Stay

Unplug and unwind at Blue Mountain Hideaway, a boutique glamping tent nestled in the woods near Shenandoah National Park and the Shenandoah River. Enjoy a real bed, a fully equipped outdoor kitchen, and complimentary firewood—no WiFi, no distractions, just the sounds of nature. Cozy up by the fire, savor slow mornings, and reconnect with what matters most. Just bring your cooler and clothes—we’ll handle the rest. Perfect for couples, solo travelers, and anyone craving a quiet place to reset.

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

4.95 out of 5 average rating, 209 reviews

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.

Guest favorite

A rustic cabin is illuminated by warm golden light from its windows, set against a soft twilight sky. The log exterior reflects the vintage charm of the structure, while the surrounding trees create a serene atmosphere, inviting guests to relax on the front porch.

Place to stay in Bentonville

4.99 out of 5 average rating, 482 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

Top guest favorite

A spacious bedroom features a queen-size bed adorned with decorative pillows. Natural light enters through a skylight and windows. A television is positioned against a wall, accompanied by a combination of vintage and modern furniture pieces, creating a cozy and inviting atmosphere.

Apartment in The Plains

4.98 out of 5 average rating, 613 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, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Guest favorite

A charming two-story home is set against a colorful twilight sky, featuring a front porch with white railings. Original stonework is visible at the base, surrounded by well-maintained landscaping, including trees and shrubs, contributing to the welcoming exterior.

Cottage in Paris

4.91 out of 5 average rating, 106 reviews

Quaint cottage in historical town of Paris VA!

Welcome to my home! This house was built in the 1820’s in the historical town of Paris, Virginia! With lots of history and character this house still has some of the original exposed beams and hardwood flooring! If you enjoy the outdoors, wineries, breweries, and shopping this is a perfect location for your stay! Minutes from the Appalachian trail, and Sky Meadows park there’s plenty of hiking around. Famous Ashby Inn restaurant just a short walk away and many more amazing places!

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

5 out of 5 average rating, 145 reviews

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.

Top guest favorite

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

4.95 out of 5 average rating, 240 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 favorite

A weathered wooden fence is presented in the foreground, supporting a round sign that reads 'The SOPER House, Est. 1964.' The backdrop features a cluster of trees with autumn leaves, and the cottage can be seen softly illuminated in the distance.

Cottage in Warrenton

4.96 out of 5 average rating, 342 reviews

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Top guest favorite

The guesthouse's exterior features sturdy stone walls and a green metal roof. White window shutters enhance the classic design. A covered porch provides a welcoming entrance, while lush green grass and neatly trimmed hedges surround the building. Scenic views of the property are visible in the background.

Guesthouse in Flint Hill

4.96 out of 5 average rating, 140 reviews

Summer kitchen guesthouse at Caledonia Farm 1812

Summer kitchen guesthouse built of stone in 1812 and located on a 115 acre free-range cattle farm on the National Register of Historic Places. The first floor is a living room with the original cooking fireplace and a kitchenette. Upstairs is a loft bedroom and bath. Housekeeping is provided on Monday and Friday mornings. Enjoy the peace and quiet, dark skies, scenic views, adventure, and culinary excellence of Rappahannock County.

Top guest favorite

A gravel driveway leads toward a stone entrance, marked by a decorative sign reading 'Cromwell's Run.' Leafless trees line the pathway, and a sweeping view of the fields beyond is visible under a clear blue sky.

Farm stay in Marshall

4.94 out of 5 average rating, 117 reviews

Middleburg Historic Country Estate/Farm Stay

8 miles from Upperville Horse Show ! Enjoy all that Virginia horse and wine country have to offer with this conveniently located country retreat. Hike at Sky Meadows, explore, attend polo matches and horse events at Great Meadow and explore the historic charm of Middleburg. The Plains, Marshall and Middleburg are hip foodie towns with amazing farm-to-table restaurants and coffee shops. . Go out or stay home, enjoy your time! !