Virginia is a must-visit state if you’re looking to explore the mountains and small towns, or spend time relaxing on the beach. Sit back and watch the action at a racetrack, delve into the state’s rich history, and unwind at a beachfront vacation rental in Virginia. Check out the state’s eight best weekend getaway spots.

1. Cape Charles

Arrange your Cape Charles weekend getaway to include some libation and food. Start with a wine tasting at Gull Hummock Gourmet Market, where you can also score some Seaside Gourmet Chocolate. Keep the party going at the Shanty with some fresh seafood on the outdoor patio. Ramble on downtown when you’re ready to stroll among the shops, such as Moonrise Jewelry, At Altitude Gallery, and Brown Dog Ice Cream. Pick up the action with Paddle Your Glass Off guided kayak tours, or schedule tee time for two at Bay Creek Golf Courses. You reach Virginia Beach on the mainland within an hour by crossing the Chesapeake Bay on Route 13.

Find vacation rentals in Cape Charles

2. Luray

Set in the spectacular Shenandoah Valley, Luray lets you choose your level of entertainment. Climb to the top of the mountain, or take a tour under it. Deep down in Luray Caverns, the Great Stalacpipe Organ transforms a section of the cave into a 3.5-acre musical instrument. When a key is played, a rubber mallet strikes a stalactite to produce a musical tone that is audible throughout the entire cavern. This attraction also features a half-mile maze that includes a misty fog, an enchanted fountain, a hidden cave, and an elevated platform. The Stalactite Cafe and the Heartpine Cafe serve fast-food style goodies. This quaint town keeps another surprise up its sleeve: your Luray vacation rental choices include tree houses, cabins, and chalets.

Find vacation rentals in Luray

Find the perfect Virginia vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

3. Chincoteague

Drop your duffel bags, grab some carry-out from Right Up Your Alley restaurant, and park yourself in the deck chair just outside your Chincoteague vacation rental to view an epic sunset on Chincoteague Bay before settling in for the night. Located on the eastern shore, this laid-back island gives you easy access to Ocean City, Maryland, which is about an hour to the north. It takes about 10 minutes to reach the access road to Assateague Island, famously known as the home of Chincoteague’s wild ponies.

Find vacation rentals in Chincoteague

4. Dublin

About 20 minutes west of Christiansburg, Dublin sits adjacent to Interstate 81 in the western part of the state. Volunteers at the Wilderness Road Regional Museum tell the story of the families who settled this area along the New River as they guide you through the exhibits, including a 19th century store. Serious mountain biking families enjoy the five-mile section of southern Virginia’s New River Trail, which is part of the rail trail corridor donated by the Norfolk Southern Railroad. Starting in Pulaski, it’s about a five-mile ride to Draper. These towns are each within a 15-minute drive from Dublin. Claytor Lake State Park is also nearby, where Claytor Lake Watersports rents boats and jet skis for fun on the water. Pick up some donuts at Olykoek Bakery to enjoy on the lake’s shore.

Find vacation rentals near Dublin

5. Clarksville

Located along the shore of Kerr Lake, Clarksville is Virginia’s only lakeside town. Look for some unique items in the funky little shops, including Doodlebug’s, Grandfather’s Country Creations, or Galleria on the Lake. As long as you’re out and about, head over to Three Sisters of Shiney Rock Winery for a tour, a tasting, and to pick out a special bottle to enjoy back at your Clarksville vacation rental. Take your place with the 5th Street crowd at Buggs Island Brewing Company, a microbrewery and pub favored by locals, travelers, and weekenders. The southeast end of the lake is about a half hour away, in Henderson, North Carolina, a larger city that offers shopping, dining, and entertainment.

Find vacation rentals near Clarksville

6. Middleburg

Middleburg covers about six blocks in the middle of Virginia’s horse country. The Middleburg Historic District makes this little gem an ideal place to see exquisite buildings from the 18th and 19th centuries. Listed on the National Register of Historic Places, the town includes the Red Fox Inn, the town’s oldest structure, established in 1728. As a foxhunting and steeplechase destination, the town is known as the Horse and Hunt Capital of the United States. The Red Horse Tavern offers indoor and outdoor dining as a fine option for casual family meals. The Red Fox Inn & Tavern serves breakfast, dinner, and weekend brunch on oak tables surrounded by handcrafted furnishings and thick stone walls. The Night Fox Pub, on the second floor, includes a full bar and casual dining. Located an hour due west of Washington, D.C., this destination lets you escape the hustle and bustle of city life while keeping you close enough to enjoy a trek into the nation’s capital.

Find vacation rentals near Middleburg

7. Staunton

Smithsonian magazine named Staunton one of the best small towns in America. Nestled in the Shenandoah Valley, Staunton’s historic buildings and country charm make it an ideal weekend getaway for sightseeing and family activities. Star B Stables’ guided horseback tours feature treks through the beautiful forests, streams, and fields, with opportunities to view local wildlife such as deer and hawks. Satisfy your thirst for cultural pursuits at the American Shakespeare Center and the Frontier Culture Museum. Stroll along the downtown streets to browse quaint shops, and venture over a couple of blocks to drop in on the Redbeard Brewing Company for a tour of the brewery and taproom.

Find vacation rentals in Staunton

8. Martinsville

Located 43 miles north of Greensboro, North Carolina, Martinsville vacation rentals incorporate the comforts of home with the picturesque scenery of the surrounding foothills of the Blue Ridge Mountains. This small town roars to life at the Martinsville Speedway, where the fans sit within a few hundred yards of the racing cars due to the small size of the track. Kid and adult drivers get to roar a little, too at Martinsville Grand Prix Go Karts nearby. For a change of pace, head over to Virginia Museum of Natural History to see exhibits that include a dinosaur gallery, fossils, and skeletons of mammals and native people. The Ten Pin Cafe inside Sportlanes bowling alley features imported beers along with snacks and sandwiches.

Find vacation rentals near Martinsville


Ready to go? Check out these amazing Virginia vacation rentals on Tripping.com.