Cottage holiday rentals in Charlottesville

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

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.

Shenandoah River Retreat

New guest cottage with gorgeous view of the Massanutten and Blue Ridge Mountains, access to the South Fork of the Shenandoah River. Sit on the porch and soak it all in, enjoy the river, and local activities King size bed, gas range/fireplace, all new appliances Wi-Fi and TV for local stations and Roku. Surrounded by farm land, bucolic setting. 4.5 miles from Merck, 2.5 miles from Coors, 3.5 miles from Massanutten Resort, 14 miles to Shenandoah National Park, 13 miles to JMU. No pets or smoking

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.

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Welcome to Towler Cottage, a getaway in the heart of Route 151 in Afton. The cottage is within minutes from the best wineries and breweries, great local trails, and the Blue Ridge Parkway! Relax in the hot tub on the rear deck, or sit out by the fire pit and gaze at the stars. Enjoy great mountain views from the front porch rocking chairs. With one bedroom with a queen bed, plus a pull-out couch in the living room, the cottage is perfect for couples. Located 25 minutes from Charlottesville.

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.

The Ivy Rose Tea House, 15 min to Cville & Mtns

Welcome to The Ivy Rose Tea House in the heart of Ivy, located just 15 minutes to Charlottesville, Crozet and Route 151 (also known as Brewery Trail). This is a unique property located on 3 acres right along Route 250. The wrap around covered deck on 3 sides offer privacy, views and a relaxing place to enjoy a meal outside or morning coffee. This character rich home was built for the guest who wants a cozy experience in the country. Fully equipped kitchen. We would love to welcome you!

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Cozy Mountain Cottage*Fire Pit*Front Porch Views

Relax with the whole family at this peaceful cottage nestled in the heart of the Blue Ridge Mountains. Short distance to Wintergreen Ski Resort, Shenandoah National Park, Blue Ridge Parkway, Skyline Drive, and the Appalachian Trail. The cottage is conveniently located in the middle of Rt 151 aka Alcohol Alley. Less than a 5 minute drive to Bold Rock Cider, Devils Backbone Brewing, Three Notch’d Brewing, and Blue Toad Cider as well as numerous other local eateries and breweries.

Honey B - Beautiful loft near UVA, Monticello

Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

Cottage in the Country (close to UVA!)

Stay at our lovely cottage beside Stonybrook stream! Only 2 miles to the city of Charlottesville. You are invited to explore the land and enjoy the brook that runs through it. Guests love the fire pit and large lawn for playing with the kids. The large, covered outdoor entertaining area is for you to use as well! Turn on the party lights and enjoy the evening. A drop in to the Rivanna river is only a mile away at Darden Towe park for tubing, kayaks and more.

The Cottage at Peavine Hollow Farm-No cleaning fee

Country chic cottage on a boutique farm in bucolic FREE UNION, 25 mins from Charlottesville or Crozet. NO CLEANING OR PET FEE. Completely remodeled cottage with well-stocked gourmet kitchen, stone fireplace (wood burning), firewood included. GE High Profile appliances and washer/dryer, granite counter tops and custom cabinets. Each bedroom has ensuite bathroom (with walk-in shower) and porch. Last mile+ is on a gravel road.