Holiday rentals in Wingina

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Acute Lodge: Boho, Romantic Getaway in Nelson Co.

Acute Lodge delivers a trendy, boho getaway in the popular destination of Nelson County. This geometric home offers privacy in the woods on just under 13 acres, but is within a 20 minute drive to breweries and 25-30 minutes to the popular Nelson 151 destination. With plenty of amenities (including fiber internet), Acute Lodge is the ultimate restorative getaway perfect for couples, friends, or even small families. Your pup is also welcome to join with added pet fee. No cats, subject to fine.

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.

WOODLAND HIDEAWAY

A private apartment in the hills of Nelson County is located in an addition to the owner's rustic home. The property is surrounded by forest and stream with a mountain view. The Blue Ridge Mountains, the James River, Wintergreen, Infinity Downs , and Charlottesville are all within easy driving distance. A great rural location, perfect for nature lovers and birdwatchers. The owners are a resource for information on the area and can provide recommendations on attractions and activities.

Shepherdess Cottage

Charming cottage located in Scottsville, Virginia on a 93 acre sheep farm. It is located 19 miles from Charlottesville. The Shepherdess Cottage is tiny, relatively private and offers beautiful views. We are a working farm so you may encounter us, but will respect your privacy as much as we can. You are welcome to "free range" with our sheep and enjoy exploring the property. Sometimes our lambing season (pretty much year-round) will offer bottle babies that you can feed and cuddle.

Ms Maria's Place - make yourself at home, relax!

Newly renovated house on a quiet cove road .2 miles off of Rte 29 between Charlottesville and Lynchburg. The property includes high speed 100 Mbps Internet, a 65" Smart TV, gas grill, and a fire pit with outdoor seating. Enjoy visiting the local restaurants, orchards, wineries, and breweries. You will be a short drive from hiking Crabtree Falls, the Blue Ridge Parkway, Humpback Rock, Wintergreen, and James River State Park. The Lovingston Winery is just minutes down the road!

Homestead at HeartRock

Welcome to HeartRock Homestead. Our sweet spot offers rustic charm and modern comfort. Come for a private grownup nature camp! A getaway for couples, friends and families. Really, there is something for everyone. AND we have great check in and check out times to maximize your stay! Have you ever heard the whippoorwill sing while watching the stars or grazed organic cut flowers amongst the morning dew or felt a seasoned sunset kiss your heart? We hope to see you soon!

Whisper Creek Lodge! Lower Level Suite!

Whisper Creek! Located in the foothills of the Shenandoah Mountains. This Lower Level Suite will provide you and friends with the perfect place for back woods peace and quiet. Located one hour from UVA, Wintergreen, numerous Craft Beer Pubs and Wineries. This includes numerous choices for hiking. If canoeing and kayaking is your interest, I am located a short distance from several launch sites. I am willing to shuttle vehicles and assist in getting you where you wanna be.

Rare Find: Private Animal Sanctuary & Tiny Cottage

For animal lovers seeking an exclusive and unique getaway, this boutique Airbnb in Scottsville offers a tranquil escape where guests can unwind in nature and connect with the sanctuary’s resident animals. Recognized by Northern Virginia Magazine, Trips 101, and Trips to Discover as one of Virginia’s most distinctive stays, this thoughtfully curated retreat features cozy furnishings, charming handcrafted details, and an expansive window that showcases views of the animals.