Holiday rentals in Sherando

Spacious Tiny Home Close to Wine, Beer & Mountains

A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most beautiful tiny house in the world. "Big Tiny", built in 2017, is a luxurious retreat that is huge on both character and amenities. This handcrafted home boasts a full-sized kitchen private bedroom, cozy sleeping loft, 2 large screen TVs, and full bath with tub. With a cathedral ceiling and walls of windows, this Escape Traveler XL is the flagship offering of the premiere tiny home builder.

Cozy Log Cabin

Relax and unwind in this secluded, hand-hewn log cabin with all the modern conveniences. 10 minutes off the Blue Ridge Parkway from mile marker 16, minutes from Shenandoah National Park and the Appalachian Trail, close to 4 breweries, 6 wineries, 3 cideries, and Wintergreen Four-Season Resort. Located on over 300 acres of private land with plenty of room to explore and enjoy the wildlife. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience.

Oasis in the Blue Ridge -Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home is located in the City of Waynesboro just a short drive from the Blue Ridge Parkway. Modern amenities, complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is all yours including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

Sunset Vista (Mountain Views) “Skies for Miles”

Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second story views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! At the entrance to Historic Waynesboro (<1 mile) and the riverside park, or its restaurants and stores to entertain even the peculiar palate or collector. Fully fenced in back yard, so bring the pups or the kids to play!

The Humble Abode Camp

The Humble Abode is a secluded CAMP & offers a scenic view of DePriest Mountains range and is the perfect place to un-plug & disconnect to reconnect!! Our private and secluded camp provides with spectacular mountain views and a NEW OUTDOOR Shower!! with pressurized ambient water temperature, spacious deck, covered porch, double bed, hammock, yard to play croquet/corn hole, private port-a-potty, charcoal grill, and a solo stove firewood pit.