Welcome to your luxurious home away from home
Tidewater Vacation Rentals offers exclusive access to luxury waterfront escapes in Talbot County and surrounding Chesapeake Bay destinations. Our dedicated team curates exceptional amenities, personalized in-home services, tailored local experiences, and seamless travel arrangements. We turn your dream vacation into an extraordinary reality.
Our exclusive property management services combine industry expertise, personalized care, and a proven track record of success to maximize your rental income while ensuring your home is cared for like our own.
Vacation Homes
Escape to the timeless elegance of Thornton Estate, a breathtaking 6,000-square-foot Manor House built in 1815, nestled just six miles from the charming town of Chestertown
6 Bedrooms | 4 Bathrooms
Chestertown, MD
Radars Landing
6 Bedrooms | Sleeps 12 | Bathrooms 3.5
Between Easton and Oxford, MD
Duck Duck Goose
6 Bedrooms | Sleeps 12
Sherwood, MD
Talbot County STR# STN-24-4 /STRN-25-14
Eagles Point Landing
4 Bedrooms | Sleeps 8 | Bathrooms 4
Oxford, MD
Nestled in a quiet, wooded area, Idlewild is a charming escape that combines rustic charm with modern comforts. Ideal for nature lovers and those seeking tranquility.
Talbot County STR# STRN-22-31
Set along the tranquil shores of Irish Creek in Royal Oak, Maryland, this charming waterfront cottage offers a quintessential Eastern Shore escape—where relaxed luxury meets natural beauty.
Unwind with family and friends in this tranquil haven—swim in the pool and soak in the water views. Make Natures Rest your next dream vacation getaway!
4 Bedrooms | 3 Bathrooms | Sleeps 8
Between St. Michael’s, and Easton, MD
Talbot County STR# STR
Welcome to Rippling Waters on Fishing Creek, a beautiful waterfront retreat on Maryland’s Eastern Shore. This family-friendly 3-bedroom, 2-bathroom home is the perfect place to relax, reconnect, and enjoy the outdoors with a private pool, deep water dock, fire pit, and kayaks.
3 Bedrooms | 1 Bathrooms | Sleeps 8
Near Blackwater National Wildlife Refuge and the Harriet Tubman Museum.
