Holiday rentals in Ivy

Cottage in Charlottesville

The exterior of the cottage features a charming white facade, accented by large windows that allow natural light to fill the interior. A welcoming wooden front door is centered in the design, with stone steps leading up to the entrance, surrounded by a manicured lawn.

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!

5.0 out of 5 average rating, 106 reviews

Guest house in Charlottesville

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.

5.0 out of 5 average rating, 151 reviews

The exterior of a brick house is framed by vibrant autumn foliage, with golden and orange leaves. A pathway of bricks leads to the entrance, and subtle landscaping includes a small tree displaying colorful leaves, contributing to a serene outdoor setting.

4.95 out of 5 average rating, 106 reviews

Spacious apt/near Charlottesville /UVA/wineries

*Spacious, sunny, 1275sf 2-bdrm apt, 9 ft. ceilings *BEDS: 1 king+2 XL twins (can convert to a 2nd king); a twin or queen air mattress avail if requested or if >4 people ($25/night pp) *cable Wi-Fi/TV *Desk+adjustable chair *15 min to UVA; close to hiking, wineries, breweries, Monticello *15 min to CHO *Panoramic views: rolling hills; lovely woods * landscaped yard; large bluestone patio *Setting along the picturesque Garth Rd. corridor *12 min. W of town; <1 mile from Foxfield Steeplechase

4.98 out of 5 average rating, 133 reviews

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries

Spacious modern house with a brand new rooftop deck overlooking Carter Mountain and Monticello. Two spacious primary bedroom suits (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood. Backs up to a lake for beautiful views from each level and tranquil environment. Convenient location - minutes away from Monticello (2 mi/4 min), downtown (2.5 mi/6 min), UVA (3 mi/9 min), wineries (3.5 mi/5 min+) & breweries.

Cottage in Charlottesville

The exterior of a charming cottage is featured, showcasing white brick walls and a sloped gray roof. Two dormer windows enhance the appearance, while a welcoming red door serves as a focal point. Well-maintained green grass and manicured shrubs surround the house, creating a friendly environment.

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.

4.91 out of 5 average rating, 458 reviews

4.96 out of 5 average rating, 138 reviews

Cabin in Charlottesville

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.

Guest suite in Charlottesville

A spacious bedroom features a wooden bed frame with a decorative pillow against a backdrop of neutral walls. Soft lighting from two bedside lamps creates a comfortable ambience. A light-colored blanket is neatly spread over the bed, while natural light enters through a nearby window.

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.

4.96 out of 5 average rating, 112 reviews

The exterior of a two-story colonial-style house is visible, showcasing a well-maintained front yard with mature greenery. A gravel driveway leads to a covered parking area. Bright blue skies and scattered clouds frame the scene, highlighting the peaceful, natural surroundings.

4.97 out of 5 average rating, 190 reviews

Wakefield Ct | Private Parking spots | Fast WiFi

Cozy stay in an updated colonial style house on a quiet street. Short drive from great local spots along Downtown Cville, UVA Corner, Monticello, Blue Ridge Parkway, The Appalachian Trail, breweries and local wineries. An excellent choice for hosting small gathering with good yard space and pouch. A wonderful stay if you like to be close to all the attractions Cville has to offer, but still far enough to enjoy peace and quiet. Thank you, for your time and consideration.

The kitchen features white cabinetry with glass-front doors and a herringbone backsplash. A farmhouse sink sits below a window, complemented by modern appliances, including a gas stove and a stainless-steel dishwasher. Natural light streams in, highlighting the spacious countertop area.

5.0 out of 5 average rating, 212 reviews

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

Fully-updated, custom home in premier location. Warm hardwoods, lots of light, comfortable sofas & beds, easy check-in -- we strive to make your stay restful and refreshing. Nestled between Scott Stadium & JPJ, O'Hill & the Rotunda, wine country & the downtown mall, you could not be closer to the action yet in a quiet, residential neighborhood. The perfect place for any & all Cville/UVA events, work trips, reunions, weddings, family vacations, college visits, etc.

Guest suite in Charlottesville

Two seated chairs are positioned on a wooden patio, facing a lush green landscape. Surrounding trees create a serene atmosphere, with sunlight filtering through the leaves, enhancing the natural beauty of the wooded setting.

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!

4.94 out of 5 average rating, 568 reviews

A panoramic view reveals rolling hills and a vibrant landscape adorned with autumn foliage. Lush green fields stretch towards the horizon, bordered by trees displaying a spectrum of fall colors under a clear blue sky.

4.95 out of 5 average rating, 144 reviews

Scenic Private Farm House Great for Large Groups

CHURCH FIELD HOUSE. Large 5 bedroom, 4 bath house with sweeping 360 degree views featuring beautiful pastoral and mountain landscapes on a 250 year old family farm in the Southern Albemarle Historic District. Enjoy large windows in almost every room with unobstructed western views. Large outdoor deck and a separate fire pit area are favorite places to view spectacular sunsets over the Blue Ridge Mountains.