Romantic Escapes & Family Fun: Weekend Trips Near DC

At Jennifer Young Homes, we know the importance of taking time to recharge, even during the colder months. Living near Washington, DC, gives you access to fantastic winter getaways, whether you’re looking for romantic retreats, family adventures, or peaceful escapes. We’ve curated a list of eight destinations with activities tailored to the season, so you can make the most of this winter!

1. Shenandoah National Park, VA

• Who It’s For: Nature lovers, couples, and peaceful retreat seekers.
• Activities: Winter hikes are magical in Shenandoah, with fewer crowds and frost-covered landscapes on trails like Hawksbill or Limberlost. Drive Skyline Drive for breathtaking mountain views under clear winter skies. Stay warm with a thermos of hot cocoa and enjoy stargazing at Big Meadows, where the crisp winter air enhances visibility. Cozy up in a rustic cabin for a serene escape surrounded by snowy woods.
• Stay: Skyland Resort or nearby mountain cabins.
• Website: www.nps.gov/shen

2. Annapolis, MD

• Who It’s For: Couples, history buffs, and foodies.
• Activities: Winter in Annapolis is perfect for exploring historic landmarks like the US Naval Academy and charming cobblestone streets without the summer crowds. Warm up with a wine tasting at Great Frogs Winery or enjoy a cozy dinner at a waterfront restaurant. Stroll through galleries and boutiques downtown, or visit the Annapolis Maritime Museum for fascinating exhibits about the Chesapeake Bay.
• Stay: Graduate Annapolis or charming waterfront inns like the Annapolis Waterfront Hotel.
• Website: www.visitannapolis.org

3. Deep Creek Lake, MD

• Who It’s For: Families, adventure lovers, and winter sports enthusiasts.
• Activities: Deep Creek Lake transforms into a winter wonderland with plenty of activities to enjoy. Go skiing, snowboarding, or tubing at Wisp Resort. Explore frozen waterfalls and serene snow-covered trails at Swallow Falls State Park. Afterward, relax by a fireplace in a cozy cabin with hot cocoa. Ice skating and horse-drawn sleigh rides are also available for some family-friendly winter fun.
• Stay: Lakefront cabins or the Lodges at Sunset Village.
• Website: www.visitdeepcreek.com

4. Charlottesville, VA

• Who It’s For: Couples, wine lovers, and luxury seekers.
• Activities: Charlottesville’s winter charm shines with indoor wine tastings at Pippin Hill or King Family Vineyards, offering breathtaking views of snow-covered vineyards. Visit Monticello for its historic winter tours and festive ambiance. Enjoy a cozy meal by the fire at local farm-to-table restaurants, or indulge in winter spa treatments at Boar’s Head Resort.
• Stay: The Clifton or Boar’s Head Resort for a luxurious winter escape.
• Website: www.visitcharlottesville.org

5. Harpers Ferry, WV

• Who It’s For: History buffs, quiet getaway seekers, and hikers.
• Activities: Take a quiet walk through the historic streets of Harpers Ferry, where you can explore museums and Civil War landmarks. Winter hikes along the Maryland Heights trail offer stunning snowy views of the Potomac River. Stop at local cafes for warm drinks and baked goods, or shop for artisan crafts and antiques in town. For a tranquil escape, cozy up in a B&B with a fireplace.
• Stay: The Town’s Inn or Cantuta Inn.
• Website: www.harpersferrywv.info

6. Rehoboth Beach, DE (Winter Edition)

• Who It’s For: Couples, foodies, and nature enthusiasts.
• Activities: Winter at Rehoboth Beach offers peaceful, uncrowded charm. Take a brisk walk along the beach and enjoy the sound of the waves in the cool winter air. Visit Cape Henlopen State Park for scenic hikes and birdwatching. Explore tax-free boutique shopping and art galleries downtown. Warm up with a gourmet meal at local favorites like Bluecoast Seafood Grill or indulge in a spa day at a nearby resort.
• Stay: The Bellmoor Inn & Spa or a cozy beachfront rental.
• Website: www.beach-fun.com

7. Lancaster County, PA

• Who It’s For: Families, couples, and Amish culture enthusiasts.
• Activities: Winter in Lancaster is magical, with sleigh rides through snowy farmland and visits to Amish markets for fresh baked goods and handmade crafts. Ride the Strasburg Railroad’s winter excursions for scenic views of the snow-dusted countryside. Families can enjoy the Hands-On House Children’s Museum or visit Dutch Wonderland’s Winter Wonderland (if available).
• Stay: The Inn at Leola Village or cozy farmhouses.
• Website: www.discoverlancaster.com

8. The Greenbrier, WV

• Who It’s For: Couples, luxury travelers, and spa lovers.
• Activities: Experience winter luxury at The Greenbrier, with activities like ice skating, sleigh rides, and indoor golf. Indulge in a full day of pampering at their world-class spa, or enjoy a candlelit dinner at one of their fine dining restaurants. Take a tour of the historic Cold War-era bunker or simply relax in front of a roaring fire with a good book.
• Stay: The Greenbrier Resort.
• Website: www.greenbrier.com

Enjoy Your Getaway! 

At Jennifer Young Homes, we know winter is a perfect time to explore local destinations and reconnect with loved ones. Whether you’re seeking a cozy mountain cabin, a quiet beach retreat, or a luxury resort, there’s something nearby to make your February unforgettable.

When you’re ready to make your dream home the starting point for all your adventures, reach out to Jennifer Young Homes. Let’s find you the perfect home base for all seasons!