Holiday houses in Ivy

The Peony Cottage in Charlottesville

This private cottage is conveniently located between Crozet and Ivy. Perfect location for accessing Monticello Wine Trail, the Blue Ridge Parkway/Skyline Drive, Wintergreen Resort, and enjoying all University of Virginia events! 3 miles from Downtown Crozet & King Family Vineyard 4.5 miles from Chiles Orchard 8.5 miles from John Paul Jones Arena 10 miles from Blue Ridge Parkway - North Entrance 30 miles from Wintergreen Resort Join us as we watch the progress of our newly planted peony field!

Pop's Cottage

Perched on a hilltop overlooking mountains, a river and cattle , POP'S COTTAGE is a fully appointed, dog friendly , one bedroom guest cottage offering a location second to none in the heart of central Virginia's wine, brewery, bourbon and cider country. Pop's Cottage is 10 miles from UVA & within 3 miles from Pippin Hill Vineyard. Wine Enthusiast named Virginia as one of the "Top 10 Best Wine Travel Destinations" in the world, so make your reservation at Pop's Cottage! Facebook & Instagram

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.

Historic HomeTract Cottage UVA/Charlottesville/Ivy

Hometract Cottage is a historic one bedroom home (NRHP, circa 1800) centrally located 15 minutes or less from Charlottesville, UVA, Crozet, Monticello, wineries and more. The cottage features ensuite bath, fully stocked kitchen, living/workspace with comfortable sleeper sofa, mature landscaping for privacy, and covered front porch. Hometract is a quiet 3-acre property with terraced garden views. Visit our chicken coop, relax in the hammock, or walk to the garden shop or Duner's restaurant.

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.

Adorable cottage steps from Grounds

A cozy Milton Grigg designed cottage and detached carriage house three minutes walk to the Lawn and ten minutes walk to the Stadium. Nestled in a wooded neighborhood. Perfect for visiting parents, UVA chapel weddings, med student rotations, and football games. NOTE: The cottage sleeps five adults and the carriage house two adults. There is one bathroom in the cottage and one in the carriage house. Please read through all the information in the 'Description' section below before booking.

Airy loft studio in the woods, 10 min to downtown

Welcome to your private stay in the woods 10 minutes from downtown Charlottesville! Located just off Rte 29 and Rte 250 on 4.7 wooded acres, this guest suite is the perfect home base for a new family as you explore UVA, Shenandoah National Park, and so much more. Ample off-street parking, a private walking trails, baby essentials and a cozy screened in porch await you at this contact-free booking. Your hosts live in the adjacent home, so anything you may need is just a knock away.

Ivy Rose Cottage nestled b/t Cville & Vineyards

The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

Rainey’s Retreat, nestled between Ivy and Crozet

Our home is nestled in between Ivy and Crozet, Virginia at the base of the Blue Ridge Mountains. We live on a private 2 acre lot that is surrounded by trees and wildlife. We have daily visits from deer, squirrels, chipmunks, rabbits, a variety of birds, and on occasion we see fox and bears. It feels very secluded yet convenient to everything. We are just 8 miles from UVA, convenient to many local wineries and breweries, and have hiking and biking opportunities all around us.

Tranquil Estate, Cottage, Vineyards and C'ville

Guests consistently say the sunsets alone are worth the stay! We've had anniversary trips, proposals, creative retreats, and gal pal gatherings looking for fun. This area boasts award winning vineyards, gardens and history buffs enjoy Monticello and Montpelier. Our peaceful cottage offers the perfect space for couples, creatives, and anyone craving beauty just 10 minutes from downtown C'ville. *Read "Your Property." Pool is available most summer stays. Thank you!

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.

Relax and Breathe In Nature at the Forest Haven!

Retreat from the stress and noise of the world for a while. Come to the Forest Haven where you can enjoy peace and quiet, yet still be just a short drive away from the restaurants and attractions in Charlottesville. Shenandoah National Park and the Blue Ridge Parkway are within an easy drive. This immaculately clean and modern apartment is located in a beautiful wooded setting surrounded by nature and wildlife. Once you get here, you may not want to leave!