Holiday rentals in Fairfield

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

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.

Tipi with a great view of the Blue Ridge Mountains

Our small family farm is conveniently located 10 minutes from Interstates 81/64 and historic Lexington, Virginia. The Tipi has amazing views of the Blue Ridge Mountains and all the wonders our little farm and community has to offers. We are convenient to many local attractions like hiking, swimming, brewery and vineyard tours and yet secluded enough to heal your stress, enjoy time with your family or simply a special time away from the grind. Come stay with us! You deserve sincere hospitality!

Cross Creek Luxury Couples Cabin

Cross Creek Luxury Couples Cabin is a one of a kind, romantic, get-away for two just 3 miles from the Blueridge Parkway. From its uniquely designed suspension over top of a creek, lighted boardwalk path through the woods that ramps up to the cabin amongst the trees giving it a true tree-house feel, 3 spacious decks for lounging and enjoying nature and the sounds of the roaring creek beneath you, to luxurious amenities galore inside and out. All in a secluded, private setting minutes from town!

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

The Maury River Treehouse

Welcome to The Maury River Treehouse. This luxury timber frame cabin sits on the banks of the Maury River. The Treehouse was built almost entirely by local craftsmen making it a true showstopper! Located 9 miles from Lexington, Washington & Lee and Virginia Military Institute. It's a fisherman's dream, paddlers paradise or just a relaxing retreat! The true timber frame construction, stone fireplace, gourmet kitchen and park like setting will take your breath away!!

Ecco Adesso Vineyards Retreat near W&L, VMI

Experience Virgina Wine Country at Ecco Adesso Vineyards! Our charming loft is perfect for a romantic escape or a spirited getaway & features panoramic views, vaulted ceilings, 2 decks, a fire pit, & all the comforts of home. Wander through the farm & explore vineyards, orchards, hiking trails, springs, and meadows or visit our on-site winery to sip & savor delicious wine. Whether you want to relax and enjoy nature or go on an adventure, you are in the right place!

Amazing Mountain Views + Hot Tub near WLU & VMI

Amazing contemporary home features a stunning mountain view from the hot tub patio and a spacious open layout filled with vintage furniture. This piece of paradise located on 6 private acres is the perfect weekend mountain escape! 15 minutes to downtown Lexington, W&L, VMI. 10 minutes to the Virginia Horse Center. Minutes from Ecco Adesso Vineyard and Rockbridge Winery. Sunrise Ridge is a pet-friendly property, we warmly welcome your pets with a pet fee of $150.

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

The Bread Barn

Welcome to Seasons' Yield Farm! Your retreat sits atop a working bakery amidst a family farm in the beautiful Shenandoah Valley. Minutes off highway 81, within 20 minutes of Lexington and Staunton. This getaway is perfect for the guest passing through or a family looking for a rural getaway. Enjoy the solitude of the country and the yield of a bakery! Custom made coffees delivered to your doorstep every morning! Check us out at Seasons' Yield Farm. Welcome!