1. Annapolis Waterfront Retreat
Drive Time: Approximately 45–50 minutes from Alexandria, VA
Location: Annapolis, MD
Standout Amenities:
Private dock for boating or fishing
Swimming pool for relaxation
Just 400 steps from the sandy beach
Spacious outdoor deck with grill
Modern kitchen and open-concept living area
Estimated Pricing: $750–$1,200 per night (varies by season and availability)
Things to Do:
Tour the U.S. Naval Academy and explore historic downtown Annapolis
Enjoy sailing or kayaking on the Chesapeake Bay
Dine on fresh seafood at local favorites like Cantler's Riverside Inn
Link: Annapolis Waterfront Retreat
2. Waterfront Estate with Pool near Easton & St. Michaels
Drive Time: Approximately 1 hour 45 minutes from Alexandria, VA
Location: Easton, MD
Standout Amenities:
Private pool with expansive waterfront views
Situated on 11 acres of serene landscape
Updated kitchen and spacious dining area
Multiple outdoor seating areas for relaxation
Close proximity to charming towns of Easton and St. Michaels
Estimated Pricing: $1,000–$1,500 per night (varies by season and availability)
Things to Do:
Visit the historic Avalon Theatre and Academy Art Museum in Easton
Explore the Chesapeake Bay Maritime Museum in St. Michaels
Enjoy biking or walking tours through the scenic countryside
Link: Waterfront Estate near Easton & St. Michaels
3. Luxury 3-Bedroom House at UVA – Outdoor Fireplace
Photo courtesy of Airbnb listing.
Drive Time: Approximately 2 hours 15 minutes from Alexandria, VA
Location: Charlottesville, VA
Standout Amenities:
Outdoor fireplace and patio area
Modern kitchen with updated appliances
Proximity to the University of Virginia and local attractions
Comfortable living spaces with stylish decor
Estimated Pricing: $400–$600 per night (varies by season and availability)
Things to Do:
Tour Thomas Jefferson's Monticello estate
Stroll through the historic Downtown Mall with shops and restaurants
Visit nearby wineries and breweries along the Monticello Wine Trail
Link: Luxury 3-Bedroom House at UVA
4. Bayberry House – Luxury, Modern, Steps to the Beach
Photo courtesy of Airbnb listing.
Drive Time: Approximately 3 hours from Alexandria, VA
Location: Virginia Beach, VA
Standout Amenities:
Modern design with luxurious finishes
Just steps away from the beach
Spacious outdoor area for relaxation
Fully equipped kitchen and open-concept living space
Estimated Pricing: $800–$1,200 per night (varies by season and availability)
Things to Do:
Walk or bike along the Virginia Beach Boardwalk
Visit the Virginia Aquarium & Marine Science Center
Explore the ViBe Creative District for local art and dining
Link: Bayberry House – Virginia Beach
5. The Gramophone – Romantic Valley Retreat
Photo courtesy of Airbnb listing.
Drive Time: Approximately 2 hours 15 minutes from Alexandria, VA
Location: Stanley, VA (Shenandoah Valley)
Standout Amenities:
Private hot tub overlooking the valley
Modern, Scandinavian-inspired architecture
Floor-to-ceiling windows with panoramic forest views
Fully equipped kitchen and cozy indoor fireplace
Secluded deck perfect for stargazing
Estimated Pricing: $300–$500 per night (varies by season and availability)
Things to Do:
Hike in Shenandoah National Park, including trails like Hawksbill and Stony Man
Explore Luray Caverns, the largest caverns in the eastern U.S.
Visit local wineries such as Wisteria Farm and Vineyard
