If you’re seeking a long weekend on the East Coast, but want to avoid the crush and chaos of NYC, you need to explore the D.C. area. Despite the stereotypes, there’s so much more to this part of the United States than the National Mall– it’s a centerpoint of U.S. history, culture, and natural beauty.
If you’re local to D.C., feel free to use this guide as a starting point for planning easily accessible long weekend getaways. And if you’re not already local to D.C., we have you covered. Our Washington, D.C. 100 Collection™ partner is Home Sweet City, which offers a range of curated city dwellings (from cozy apartments to luxe mansions). Home Sweet City’s beautiful rentals are thoughtfully located in desirable D.C. neighborhoods so you can stay close to significant landmarks and great food while still enjoying the privacy of a residential area.
So once you’re done touring the monuments, keep exploring– there’s plenty to enjoy within a 5 hour drive of D.C.
We’re shining the spotlight on five curated, 100 Collection™-approved locations you won’t want to miss. Book one, or plan to hit all of them to really immerse yourself in this underrated area of the United States.
Distance from Washington, D.C.: Approximately 2.5 hours
Charlottesville, Virginia, is a small city tucked away in the foothills of the Blue Ridge Mountains. Praised for its wineries, historic sites, and arts scene, there’s no shortage of things to do. Start with Monticello, Thomas Jefferson's former estate. The grounds alone are worth the trip. From there, check out James Monroe's Highland just down the road, or walk the University of Virginia campus– Jefferson designed it, and it's a UNESCO World Heritage Site. The Downtown Mall is one of the longest pedestrian malls in the country, and it's the heart of the city. Live music fills venues like the Jefferson Theater and the Paramount Theater on any given weekend. Charlottesville is also the center of Virginia wine country.
Over 30 wineries sit within a short drive, and the Monticello Wine Trail is the best way to explore them. King Family Vineyards and Pippin Hill Farm & Vineyards are two favorites– the wine is great, and the Blue Ridge views from both are hard to beat. When you're hungry, The Alley Light is a speakeasy-style spot hidden behind a bookshop (yes, really), and MarieBette Café & Bakery does French-inspired pastries and brunch that locals swear by.
Stay Charlottesville, our 100 Collection partner in the area, offers an eclectic mix of chic condos, spacious estates, and beautiful antique houses that capture the historic feel of the area. Whether you want a cozy in-town base or a sprawling country estate, these are the ones to look at:
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Distance From Washington, D.C.: Approximately 2.5 hours
Calling all outdoor enthusiasts! Massanutten sits just minutes from the Shenandoah Valley, offering stunning views of rolling mountains. This one's for the outdoor crowd. Massanutten Resort is the anchor of the area, and there's something going on every season– skiing and snowboarding when it's cold, the indoor WaterPark and golf courses when it warms up.
One of the popular places to visit is Shenandoah National Park. Dark Hollow Falls and Rose River Falls are the kind of waterfalls that stop you in your tracks. The trails range from easy strolls to full-day hikes, and Skyline Drive– the 105-mile scenic road through the park– is one of the best drives on the East Coast. Come in fall and the foliage alone is worth the trip. Beyond the park, Luray Caverns is one of the largest cave systems in the eastern U.S. The underground formations are wild, and the Great Stalacpipe Organ– an instrument that plays music using the cave's actual stalactites– is something you just have to hear for yourself.
Book your mountain getaway with The 100 Collection's partner, Vacation Properties Made Simple. Their collection of gorgeous cabins and lodge-style homes provides the perfect setting to unplug and immerse yourself in Virginia’s beauty. After a day on the trails or the slopes, you want somewhere that actually feels like a retreat– and their cabins and lodges deliver
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Distance from Washington, D.C.: Approximately 3 hours
Head to Ocean City, Maryland, to eat your fill of seafood and unwind on the beach. Ocean City has a nostalgic East Coast feel thanks to its iconic boardwalk and old-school amusements. Snag an ice cream, wander into taffy shops, watch street performers, or hop on the Ferris wheel– whether you're 9 or 99, there’s something for kids of all ages.
The crab cakes here are the real deal. Fager's Island is a local go-to for sunset dining with views of the Isle of Wight Bay, and The Shark on the Harbor does great waterfront seafood without the tourist markup. If someone in your group doesn't eat seafood, don't worry– there are plenty of other options around town.
Off the boardwalk, rent a kayak or paddleboard and explore Assawoman Bay. Deep-sea fishing charters run all year. Northside Park offers great bay views and hosts events year-round, including the Winterfest of Lights. Golfers should look into Eagle's Landing Golf Course. And if you time it right, the annual Sunfest and the White Marlin Open (the world's biggest billfish tournament) are experiences that stick with you.
When you’re planning your Ocean City trip, you’ll find beautiful options for every group size with our 100 Collection partner, Seaside Vacations & Sales. They offer well-lit, cozy houses, townhouses, and condos right on the water. Here's where to book your stay in Ocean City:
Distance from Washington, D.C.: Approximately 3.5 hours
Let the wild horses of Chincoteague, Virginia, drag you away. Seriously! Chincoteague is famous for its wild pony herd. If you (or your kids) love ponies, book your trip for late July– the annual Pony Swim and Auction has been a tradition since 1925. Watching the ponies swim across the Assateague Channel is one of those moments that stays with you. The Chincoteague National Wildlife Refuge, on the southern end of Assateague Island, covers 14,000 acres. Rent a bike and ride the Wildlife Loop Trail early in the morning when the island is quiet, and the wildlife sightings are at their best. The Assateague Lighthouse, built in 1867, gives you panoramic views across the island and out to the Atlantic from the top.
Chincoteague’s culinary scene offers fresh seafood and other local East Coast eats, ranging from savory sandwiches to sweet baked goods. AJ's on the Creek is a standout for waterfront dining, and Island Creamery has been drawing crowds with handmade ice cream flavors for years– it's the kind of place where you'll end up going back twice in one trip.
Seaside Vacations & Sales is also The 100 Collection’s partner for Chincoteague (as well as Ocean City). Each airy island villa or house has its own fresh, comfy, and have that coastal feel you want on an island getaway– the kind of places where sand between your toes is part of the charm, not a problem.
Distance from Washington, D.C.: Approximately 4.5 hours
The Pocono Mountains are an ideal destination for outdoor sports enthusiasts. Summer means rafting and kayaking on Lake Wallenpaupack (one of Pennsylvania's largest lakes) and the Lehigh River Gorge. Winter means skiing, snowboarding, and snow tubing at Camelback and Jack Frost– followed by hot cocoa, obviously.
But the Poconos aren't just about outdoor sports. Jim Thorpe is a small town often called the "Switzerland of America" for its mountain scenery and Victorian architecture. Take the Lehigh Gorge Scenic Railway for a ride through the gorge, then explore the town's antique shops, art galleries, and restaurants on foot. Bushkill Falls, known as the "Niagara of Pennsylvania," has eight waterfalls connected by hiking trails and bridges. If you want some adrenaline, Pocono TreeVentures runs an aerial adventure course that's a hit with families and groups.
The food scene here has come a long way. You can visit Barley Creek Brewing Company, which Barley Creek Brewing Company is a local favorite for craft beer and pub food. The Stroudsburg area has a growing restaurant scene worth exploring too, with farm-to-table spots and local bakeries mixed in alongside classic mountain cookhouses.
Pocono Mountain Rentals, our 100 Collection partner, offers large mountain houses that combine cabin-like coziness with seriously upscale amenities (like luxe stainless-steel kitchens with ample countertop space, hot tubs, and fireplaces). Here are top guest favorites from their mountain cabin homes.
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Harpers Ferry sits at the intersection of the Potomac and Shenandoah rivers, making it a prime spot for both history enthusiasts and outdoor adventurers. This small West Virginia town is home to Civil War sites, miles of hiking trails, and water activities all within walking distance. Spend your mornings exploring the historic Lower Town's museums and shops, take an afternoon kayaking trip down the Potomac, or hike a portion of the Appalachian Trail that runs right through town. The area offers excellent rock climbing spots and mountain biking trails for those seeking more exhilarating activities.
The historic Lower Town is preserved as part of Harpers Ferry National Historical Park, and the history here runs deep. This is where abolitionist John Brown launched his famous 1859 raid, and where the Niagara Movement (a precursor to the NAACP) held its first U.S. meeting in 1906. In the afternoon, kayak the Potomac or hike the Maryland Heights Trail– the overlook at the top is one of the most photographed spots in the mid-Atlantic. For more action, River Riders runs guided whitewater rafting, tubing, and zip-line tours. Rock climbing at Maryland Heights and Loudon Heights draws experienced climbers, and the mountain biking trails are solid. If you'd rather take it easy, the town runs regular ghost tours, and the restaurants along High Street are better than you'd expect for a town this size. The Anvil Restaurant and Hamilton's are two worth trying.
Mountain Mama, our 100 Collection partner in Harpers Ferry, began when owners Eddie and Mary discovered their own perfect escape here. Their properties feature scenic valley views, outdoor firepits, and screened porches that let you soak in the surroundings. You'll feel at home the second you walk in.
Distance from Washington, D.C.: Approximately 3.5 hours
Here's what we love about Virginia Beach - it doesn't try too hard! Three and a half hours from D.C. gets you to a place where you can still find parking, the seafood is legitimately fresh, and the beaches have room to breathe.
Skip the main tourist strip and drive down to Sandbridge Beach. It's quieter, the houses are beautiful, and you get that "found a hidden gem" feeling even though it's been there all along. First Landing State Park is right there, with cypress swamp trails that feel like they belong in a different part of the country. The Military Aviation Museum has rare World War I and World War II aircraft that still fly– you won't see these anywhere else. The Virginia Aquarium & Marine Science Center is a hit with families, especially their seasonal dolphin-watching boat tours.
For food, skip the chains and head to where the fishing boats actually unload. Spots along Rudee Inlet are where the real Virginia Beach happens. Back Bay National Wildlife Refuge, just south of Sandbridge, has miles of undeveloped beachfront, kayak trails through coastal marshes, and some of the best birding on the East Coast. Visit in fall or winter, and the migratory bird numbers are wild. Over on the main strip, Neptune's Park and the ViBe Creative District are worth your time.
Siebert Realty vacation rentals have pampered their clients for years. These aren't your typical beach rentals - we're talking about homes with kitchens that work perfectly for big groups (double ovens, multiple fridges, counter space that makes sense), and living areas where everyone can spread out without feeling cramped. The outdoor spaces are what really wow guests. Some have pickleball courts, which has quickly become popular over the years. The best part? You're steps from sand that's rarely crowded, even in summer!
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As you map out your D.C. area itinerary, we encourage you to plan your destinations thoughtfully so you can make the most out of your trip.
If you’re already a D.C. resident or you live close by, consider carving out a long weekend for yourself and your loved ones sometime soon.
Or, if you’re farther away, we suggest planning a few days at each location– there aren’t many other places where you’re a stone’s throw away from the forest, the beach, and tons of historic landmarks.
Curious about the other curated destinations in The 100 Collection™?
