House holiday rentals in Charlottesville

The Cherry Tree, downtown estate, 8 parking spaces

Excellent downtown location & beautifully restored historic home within walking distance to the downtown mall, Main Street shops, and restaurants. Incredible attention to convenience details such as a wired conference room table, plumbed coffee machines, and a power strip next to every seat and bed. No need to compromise with small rooms or fight for bathrooms. Enjoy a bathroom to every bedroom and more than plenty of space, seating, and sleeping for 16 people. Come isolate in comfort and style.

West Wing

Quiet West Wing of my home, was newly renovated February 2020. The West Wing has a private entrance set in a mature garden. Two bedrooms upstairs sleep up to four people. One w/queen size bed and views of the garden.The 2nd has 1 full and 1 twin bed, plus walkout balcony. Each floor has a full bath. The 1st floor has a combined living room/dining area with a counter, bar sink, microwave, coffee maker, toaster oven andTV. Pet dogs only are welcome. The cleaning fee is included in the base price

Cottage just off Main St.

2 Bd/1 Bath - Walk to Charlottesville’s best restaurants/bars/bakeries on Main Street (3 min. walk - one of the closest you'll find)! Pets welcome with a Reasonable $25/pet fee, no extra $,fenced back yard! Walk to UVA (20 min), UVA hospital (15 min), the Downtown Mall (10 min), or the Amtrak train station (5 min)! One off-street parking spot, with additional paid parking available at the Amtrak parking lot (3/12/50 per hour/day/week, ~3 min) Please make sure to review all photos/descriptions.

One Level Living at Shadwell Terrace

Set in the heart of Wine Enthusiast’s Wine Region of the Year, this newly renovated 2-bedroom, 800 sq/ft terrace level flat with separate entrance, is located in a private setting in the Keswick area. Close to Downtown Charlottesville, we are adjacent to Clifton Inn and Glenmore and minutes to Keswick Hall. After exploring many of Virginia’s wineries, breweries, and historical sites, kick your feet up between the trees in the hammock or share your adventures online with our high speed Wi-Fi.

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

Belmont Private Suite, 1/2 mile to Downtown Mall

Cozy, quiet high-ceiling basement suite located in historic Belmont neighborhood. Private entrance with keypad lock for easy check-in/out. Space includes living area, 1 large bedroom with queen bed (air mattress provided if needed), full bathroom with towels/essentials, coffee maker, electric tea kettle, microwave and mini fridge. Walking distance to Downtown mall and numerous restaurants, coffee shops, and parks nearby. 1-2 mile walk from UVA and 3 miles to Monticello. Free street parking.

Woodwind Cottage

Woodwind Cottage is a brand new, beautifully built cottage with living room, bedroom, bath, kitchen and loft. It has charming architectural details and a covered porch for enjoying the view of the woods. The loft has a fold out sofa for an extra guest or private work space. The home has wifi, smart tv for streaming, and a gas fireplace. Enjoy reading in the oversized window seat, rise early to see deer in the yard or, perhaps, a hot air balloon overhead in the spring and fall.

Unit 1_Expansive Luxury Suite for up to 4 Persons

Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.

The Pop Inn | Perfect for your group getaway

Welcome to The Pop Inn! This renovated Victorian has been designed for fun with guests in mind. Located in a desirable residential neighborhood, you can safely walk to the historic downtown area or use the house as your jumping off point for vineyard/brewery tours. Whether you're visiting the area for a bachelorette party, wedding, couples' getaway, or family retreat, The Pop Inn is the perfect place to stay to experience the beautiful Charlottesville (aka C'ville) area!

Hidden Haven

Hidden Haven is just that! A 600 square foot romantic, private, peaceful, little haven. Hidden in the woods just 6 miles outside of the Town of Orange. Open the garage door in the living area and step out on the 300 square foot screened in porch where you can relax at the firepit under the covered roof. On the porch at Hidden Haven, we like to say, "time wasted is time well spent". The romantic vibe and modern amenities make it a prefect place for a couple's getaway.

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.