
Vacation rentals in Simmons Gap
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Top-rated vacation rentals in Simmons Gap
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Duck Inn B&B at Small Axe Farms
Unique private space on our small family farm. Relax on our large deck, walk our property, or explore the local area. Option to add homecooked breakfast and dinner. Great location : 8 mi to Massanutten (snow sports, arcade, golf, waterpark, mountain biking); 5 mi to Shenandoah Nat'l Park (hike, scenic cycling/drive); 4 mi to Shenandoah River (fish, kayak, rafting, tubing); 3 mi to Elkton (award-winning brewery, excellent local restaurants, and shops); 20 mi to JMU, 35 mi to Charlottesville/UVA

Moss Vineyards Lodging
We welcome you to our new modern house (2020) located on 52 private wooded acres, adjacent to our winery and the Blue Ridge. Designed and built by award winning Architect and wine maker, Barry Moss, it is gorgeous inside and out. Decks overlook the river, forest and mountain farms. A path leads down to the river beach. Walk up to the top of the mountain and experience the best wines and views of any winery in Virginia. Modern interiors with wood floors, granite counters, and tiled bathroom.

Whippoorwill Way Cabin with Mountain Views
5 star host of Rabbit Hollow cabin, presents this completely renovated mountain cabin, secluded retreat for couples or families. Walking distance to Shenandoah National Park, spectacular mountain views from spacious deck. State of the art kitchen , granite counter tops, master suite with king bed, and bathroom with charming mural. Warm up by wood burning stove. Lower level holds second bedroom with brand new queen bed, bathroom and living area with trundle bed sleeps two and electric fireplace.

Idyllic Cottage Retreat
⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

Mountain View Cabin
Take it easy at this unique getaway in the beautiful Appalachian Mountains. Our cabin provides you with a peaceful stay and a once in a lifetime experience. It sits on privately owned land with 96 acres of farm, hills, and mountains. You can enjoy your morning coffee on our covered porch while watching the cows graze. Our cabin is within 10 miles of the area’s popular attractions: Shenandoah National Park & Massanutten Resort. We have everything you need for a memorable stay in the Valley.

Shenandoah Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Shenandoah Yurt is a one-of-a-kind luxury retreat perched in the serene seclusion of the mountains. You’ll find no compromises with respect to premier cabin-like construction, modern amenities, a hot tub, wood-burning stove, archery, EV charger, sizable elevated deck, pool table, board games and so much more! This extraordinary stay is surrounded by the colorful environs of Shenandoah National Park at an elevation of over 2,500 ft! Experience #YurtLife—just 2 hours away from Washington DC!

Shenandoah Stargazer with Sauna
Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Little Forest Tiny Cottages in Free Union
Enjoy the breathtaking views of the Blue Ridge Mountains on this 26 acre Olde English Babydoll Sheep farm right from your window. Our farm is a haven of peace and serenity in a secluded but centrally located area just 18 miles northwest of Charlottesville. Wake up to delicious farm fresh breakfast from our eco-friendly farm. Take pictures of fluffy sheep and angora rabbits grazing on rolling hills. Hike our private trail. Breathe in the fresh mountain airs. Sleep in. Slow down. Relax.

Blue Ridge Retreat 2 w/ Hot Tub/Sauna/Cold Plunge!
BNB Breeze Presents: Blue Ridge Mini Lux Retreat 2! Experience the Shenandoah Valley and the beauty of the Blue Ridge Mountains from our newly-built retreat! With a private hot tub, sauna, fire pit and cool pool, the only thing that makes this retreat better is the incredible and picturesque views of the Blue Ridge Mountains that you get with your personal retreat in paradise! Your extensive amenity list includes: • HOT TUB! • Sauna • Fire Pit • Cool Pool • Grill • Picturesque Views

Parker Mountain Carriage House Near SNP, UVA & JMU
Serene country living just 12 miles to Shenandoah NP & 19 miles to UVA. 3.7 miles to Blue Ridge School. 35 miles to JMU, Harrisonburg. Enjoy beautiful mountain views, sunrises/sunsets from your own patio on 12 acres surrounded by mountains & 300 acre cattle farm. Wineries, Dining & Shopping are only minutes away. Peace & quiet, acres to explore, Parker Mountain Carriage House is above the garage, connected to the main house. We respect your privacy & are available as needed.

Amazing Escape: 3,000ft Views w/ firepit + WiFi
Fall in love with this cabin through one of the most awe-inspiring sites in the US: an endless blue-green mountain majesty. With unimpeded views of the Blue Ridge Mountains from 3300 feet of elevation, you'll be able to escape from any daily stresses. The fall foliage provides a wonderful leaf peeping experience. Waking up and to breathe in the fresh mountain air, cozy up near the indoor fireplace with a cup of coffee. That is just a small slice of our paradise on the mountain.

CloudPointe Retreat
Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.
Popular amenities for Simmons Gap vacation rentals
Other great vacation rentals in Simmons Gap

Secluded LUX Bunker | Hot Tub, Views & Trails

Elkton Dairy Barn near Shenandoah National Park

The Crooked Cabin

The Oak Tree House-Hot Tub, Firepit, Mtn Views!

Hummingbird's Rest - A Luxury Wine Country Retreat

Shifflett's Ole Homeplace - serene river getaway

Shenandoah River Retreat

Family Retreat @ Elkton, Hot tub, stocked pond
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- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- Bryce Resort
- University of Virginia
- Early Mountain Winery
- Wintergreen Resort
- Monticello
- James Madison University
- Devils Backbone Brewing Co Basecamp
- Glass House Winery
- Cardinal Point Winery
- Blenheim Vineyards
- Prince Michel Winery
- Shenandoah River Outfitters
- The Rotunda
- Frontier Culture Museum
- John Paul Jones Arena
- James Monroe's Highland
- Downtown Mall
- Shenandoah Caverns
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park





