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Things to Do in Charlottesville

Discover seasonal activities and local experiences near your Virginia Guesthouses rental.

Seasonal Activities

Explore Year-Round

From winter to fall, Charlottesville offers something for every season and interest.

Tell Me About It Tours

Tell Me About It Tours

Charlottesville ghost and mystery tours for ages 8 and up, available as self-guided downloads or private in-person group experiences lasting about 2 hours.

Spring Creek Golf Club

Spring Creek Golf Club

Spring Creek Golf Club in Zion Crossroads offers a challenging course open to members and the public, located 20 miles east of Charlottesville.

Rick Britton's Navigator Tours

Rick Britton's Navigator Tours

Guided historical tours of central Virginia led by Rick Britton, covering Civil War battles, presidential sites, and University of Virginia landmarks.

Old Trail Golf Club

Old Trail Golf Club

Play an 18-hole championship golf course in Crozet with stunning Blue Ridge Mountain views at Old Trail Golf Club.

Oasis Day Spa

Oasis Day Spa

Oasis Day Spa offers personalized spa services including massages, facials, manicures, pedicures, and waxing in Charlottesville.

Neroli Med Spa

Neroli Med Spa

Neroli Med Spa in Charlottesville offers massage, aromatherapy, skincare, and spa treatments for a relaxing vacation experience.

Meadowcreek Golf Course

Meadowcreek Golf Course

Public golf course in Charlottesville offering affordable rates and walking options for all skill levels.

James Monroe's Highland

James Monroe's Highland

Explore Highland, the historic home of James Monroe, fifth U.S. President, located in Charlottesville near William & Mary.

Halo Salt Spa

Halo Salt Spa

Halo Salt Spa in Charlottesville offers salt therapy, massage, infrared sauna, and yoga for relaxation during your vacation.

Cville Tours

Cville Tours

Explore Charlottesville with Cville Tours' expert local guides offering Civil War history, craft beer, wine, and culinary experiences.

Cityspa Day Spa

Cityspa Day Spa

Cityspa Day Spa in Downtown Charlottesville offers expert skin care, massage therapy, body treatments, and reflexology services.

Central Virginia Wine Tours & Transportation

Central Virginia Wine Tours & Transportation

Explore Central Virginia's wineries, breweries, cideries, and distilleries with safe, reliable transportation from Orange VA for couples to groups of 20.

Birdwood Golf Course

Birdwood Golf Course

Birdwood Golf Course at Boar's Head Resort offers an 18-hole championship course, 6-hole Par 3 course, and putting green in Charlottesville.

Ablemarle Charlottesville Historical Society Walking Tours

Ablemarle Charlottesville Historical Society Walking Tours

Explore Charlottesville's rich history with trained guides on walking tours covering Court Square, local heritage, and more year-round.

Charlottesville Area Activities

Charlottesville Area Activities

Discover Charlottesville activities including Blue Ridge hiking, vineyard tours, Shenandoah National Park, and historic Founding Father homes.

The Virginian

The Virginian

Discover The Virginian, Charlottesville's oldest restaurant since 1923, serving Southern fried chicken, steaks, and classic comfort food on The Corner.

Virginia Discovery Museum

Virginia Discovery Museum

Explore hands-on learning at Virginia Discovery Museum in Charlottesville with two galleries and 15 interactive play areas designed for children.

Trump Winery

Trump Winery

Visit Trump Winery on the Monticello Wine Trail in Charlottesville for wine tastings, gourmet cuisine, and vineyard views.

Three Notch'd Brewing Company

Three Notch'd Brewing Company

Tour Three Notch'd's Charlottesville production brewery and enjoy craft beers, beer-infused cuisine, and cocktails on the outdoor patio.

Thatch Winery

Thatch Winery

Explore Thatch Winery near Charlottesville, Virginia, featuring 60 acres with tasting bars, gardens, patios, and scenic terraced decks.

Starr Hill Brewing

Starr Hill Brewing

Explore Virginia's second oldest craft brewery with year-round and seasonal beers, located in Charlottesville and Crozet near Guesthouses rentals.

The Southern Cafe & Music Hall

The Southern Cafe & Music Hall

Live music venue in downtown Charlottesville featuring local, regional, and national artists across multiple genres with an on-site café.

South Street Brewery

South Street Brewery

South Street Brewery is a friendly neighborhood brewpub in Charlottesville since 1988, featuring craft beers and local artisan food.

Shenandoah National Park

Shenandoah National Park

Explore Shenandoah National Park's 200,000 acres with hiking, cycling, wildlife viewing, scenic drives, and ranger programs.

Rivanna River Company

Rivanna River Company

Paddling outfitter near Charlottesville offering kayak, canoe, and paddleboard rentals with guided and self-guided trip options for all skill levels.

Reason Beer

Reason Beer

Reason Beer is a 30-barrel craft brewery in Charlottesville featuring lagers, IPAs, porters, stouts, and blonde ales in a welcoming taproom.

Public Fish & Oyster

Public Fish & Oyster

Fresh fish and raw oyster bar in Charlottesville featuring daily fish specials, steampots, and clam chowder for seafood enthusiasts.

Pro Re Nata Farm Brewewry

Pro Re Nata Farm Brewewry

Craft brewery and cidery in Crozet with Blue Ridge Mountain views, live music events, and a scenic patio for drinks and relaxation.

Prince Michel Winery

Prince Michel Winery

Visit Prince Michel Winery in Leon, Virginia for wine tasting, craft beers, live music, and pet-friendly weekend patio gatherings.

Pollak Vineyards

Pollak Vineyards

Family-owned winery near Charlottesville offering estate-grown wines, snacks, and picnic grounds in a stunning vineyard setting.

Monticello

Monticello

Explore Thomas Jefferson's historic Monticello estate with self-guided tours, private tours, and family scavenger hunts in Charlottesville.

Market Street Wine

Market Street Wine

Independent wine, beer, and gourmet shop in Charlottesville offering personalized recommendations and 10% off for Guesthouses renters.

Live Music

Live Music

Discover live music venues in Charlottesville, including the historic Jefferson Theater and Southern Cafe & Music Hall, perfect for your vacation rental stay.

Lampo Neapolitan Pizzeria

Lampo Neapolitan Pizzeria

Experience authentic Neapolitan pizza at Lampo in Charlottesville, featuring traditional recipes with premium ingredients and delicious desserts.

King Family Vineyards

King Family Vineyards

Explore King Family Vineyards, a family-owned winery in Crozet, Virginia, just 15 minutes from Charlottesville offering wine tastings and vineyard experiences.

Jefferson Vineyard

Jefferson Vineyard

Explore Jefferson Vineyard in Charlottesville, an award-winning winery with historic roots and beautiful outdoor tasting spaces.

The Jefferson Theater

The Jefferson Theater

Historic 1912 concert venue on Charlottesville's Downtown Mall featuring live music, restored architecture, and two full bars year-round.

Grace Estate Winery

Grace Estate Winery

Visit Grace Estate Winery in Crozet near Charlottesville for wine tasting, vineyard tours, mansion exploration, and patio dining experiences.

Glass House Winery

Glass House Winery

Glass House Winery in Free Union offers artisan wines and handcrafted chocolates with a tropical vibe near Charlottesville.

Duner's Restaurant

Duner's Restaurant

Fine dining with a casual vibe in Ivy, Virginia, featuring a daily-changing menu with seasonal ingredients and creative chef-driven cuisine.

C&O Restaurant

C&O Restaurant

Fine dining destination in Charlottesville run by chef Dean Maupin, featuring seared halibut, blackened salmon, glazed duck, and decadent desserts.

Champion Brewing Company

Champion Brewing Company

Visit Champion Brewing Company's Charlottesville taproom for craft beers, games, and casual food on an outdoor patio.

Castle Hill Cider

Castle Hill Cider

Visit Castle Hill Cider in Keswick, Virginia for on-site apple tastings, scenic grounds tours, and events like yoga and cheese classes.

Boylan Heights

Boylan Heights

Boylan Heights is a UVA sports bar in Charlottesville specializing in organic beef burgers, cold drinks, and milkshakes with multi-level seating to watch games.

Bold Rock Tap Room at Carter Mountain Orchard

Bold Rock Tap Room at Carter Mountain Orchard

Visit Bold Rock's award-winning craft cider tap room at Carter Mountain Orchard near Charlottesville, featuring scenic orchard views and the full cider portfolio.

Blue Mountain Brewery

Blue Mountain Brewery

Blue Mountain Brewery in Afton, VA serves signature craft beers and seasonal brews at their brewpub with on-site dining since 2007.

Blenheim Vineyards

Blenheim Vineyards

Explore Blenheim Vineyards in Charlottesville, Virginia, featuring 100% Virginia-grown wines from 32 acres of historic estate vineyards established in 2000.

Bang!

Bang!

Bang! serves Asian-inspired tapas with dumplings, steamed buns, and craft cocktails in Charlottesville, Virginia.

The Alley Light

The Alley Light

The Alley Light offers casually elegant French-inspired small plates, craft cocktails, and curated wines from small wineries in Charlottesville.

Ace Biscuit & Barbecue

Ace Biscuit & Barbecue

Southern-style barbecue and breakfast spot in Charlottesville led by chef Brian Ashworth, featuring pulled pork, brisket, fried chicken, and custom biscuits.

Ablemarle CiderWorks

Ablemarle CiderWorks

Visit Ablemarle CiderWorks near Charlottesville for apple orchard tastings, ciders, live music, and trivia events in North Garden, Virginia.