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

Spacious modern house with a large furnished rooftop deck overlooking Monticello & Carter Mountain. Not one, but two spacious master suites (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood and backs up to a lake for beautiful views 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 (closest: 3.5 mi/5 min) &breweries.

5BR-Pool-Hot Tub-Pond-FirePit *19 mins to UVA*

Imagine staying in a home in beautiful central Virginia right in the heart Wine Region of the Year surrounded by hundreds of vineyards, breweries, & cideries, not to mention incredible historic sites and popular stops like UVA, and not ever wanting to leave the house! Welcome to Minicello! Named after nearby Monticello (home of Thomas Jefferson, just 5 minutes away), this 5-bdrm has it all. Private saltwater pool, 5-person hot tub, stocked fishing pond, pool table are all yours during your stay!

Spacious & Private Great for Groups &Winery Lovers

Located just outside of Charlottesville, this country getaway offers peace and quiet AND proximity. Within 30 minutes, you can be at 10 wineries, historic Monticello, downtown Charlottesville, UVA, or Carter’s Mountain Orchard. No matter what type of getaway you’re looking for, it is accessible from the Creekside Cottage! With 5 bedrooms, 3.5 baths, 3 living areas, 2 dining areas, a full kitchen, and laundry, this is a home away from home where you can live comfortably. *Must be 21+ to book!

Dogwood Cottage

The Fork Union Motor Lodge on Route 15 accommodates up to three people in two bedrooms. With one bathroom featuring a walk-in shower, it provides an ideal spot to rest during a trip down Route 15. Perfect for overnight guests visiting the nearby Fork Union Military Academy. The house is designed like a motel and includes a kitchenette with a microwave and oven, though there are no pots and pans. Coffee and tea are available, and a nearby grocery store offers prepared foods for easy prep.

Homestead Haven of Keswick

Step into our farms original 1930s homestead & experience a blend of historic charm and modern comfort. Nestled among lush greenery, veteran oak trees, and beautiful crepe myrtle trees. Relax in the spacious, fenced-in backyard under wide open skies, complete with a classic tire swing that brings back the joy of simpler times. Homestead Haven offers plenty of room to roam, inside & out. Sip your morning coffee on the cozy front porch, explore Cville, or unwind in the peaceful atmosphere.

Country Living - 18 min to Downtown C'Ville

Located on a dead-end road with only local traffic, enjoy the peace and tranquility our home has to offer with an easy drive to Charlottesville or Richmond as well as DC. With approximately 2100 square feet, you will be able to spread out comfortably! Three bedrooms, 2.5 bathrooms await your stay! We are an easy 20-21 minutes to UVA Grounds/"The Corner" and 18 minutes to Downtown Charlottesville. Please reach out to me with any questions! We look forward to hosting you.

Unwined in Monticello

Relax with the whole family at this peaceful place to stay. Nestled on 2.5 quiet acres this single level home provides space and tranquility as well as easy access to several stops on the Monticello Wine Trail. Blenheim Vineyards, Trump Winery and Mt. Ida Tasting Room and tap house all within 5 miles with several other award winning wineries very nearby. Carter Mountain Orchard is just 11 miles away for some outdoor family fun.

1893 House on Wild Oats Farm

This traditional rambling farm house built in 1893 is located on a 130 acre working cattle farm in lovely rural Virginia. Enjoy your morning coffee with views of the pastures, pond and woods from 3 porches. The farm is conveniently located to Scottsville, Charlottesville, UVA, Monticello, Ashlawn Highland, the James River, Richmond, Mt. Ida and award winning winery's and breweries. 8 people max staying in house

10 Wineries Within 10 Miles & Nigerian Dwarf Goats

Upscale boutique Carriage House on a 25-acre farm in Charlottesville Wine Country. Just minutes from top vineyards, this light-filled retreat features elegant rustic design, new furnishings, and spa-like comfort. Enjoy visits with Nigerian dwarf goats and free-ranging chickens—plus fresh eggs in season. Perfect for romantic getaways or remote work, with WiFi, cozy touches, and the beauty of nature all around.