4 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
Summary:Experience the ultimate Chesapeake Bay getaway on Tilghman Island! This stunning waterfront retreat will feature a brand new pool ready for Summer 2026, perfect for relaxing, soaking up the...
Created Jul 20, 2026
6 Br Private Vacation Home Vacation Rental In Wittman, Maryland
Escape to Bayview 2.0, a stunning waterfront retreat within a few miles of charming St. Michaels. Designed for unforgettable getaways, this expansive estate comfortably hosts up to 12 guests on a...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Tilghman Island, Maryland
STRN-23-58Simplicity Cottage is a circa 1920 Waterman's Cottage. Wide water views and bay breezes! This fantastic 1920's Waterman's cottage has the charm and waterfront location that is hard to...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
Big Amenities: Pool Hot Tub Amazing Views!Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and views that go on and on, you can stake your claim to this spot and relax...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Escape to Tilghman Island, a historic Chesapeake Bay community known for its working waterfront, friendly locals, and quiet pace of life. This charming cottage offers a comfortable,...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
Talbot County STR License #STN-22-20This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-filled interior and contains a first-floor bedroom and a flow-through...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
Furnished Sunroom | Family Friendly | Half-Mi to MarinaMake your way to this lovely Tilghman Island vacation rental, ideal for a trip filled with sailing, fishing, and savoring the areas fresh...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Wake up to sweeping Chesapeake Bay views just minutes from St. Michaels. Cast a line from your private dock, sip coffee on the deck at sunrise, and end the day with spectacular sunsets over...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Tilghman Island, Maryland
The Tilghman Island Point of View is a waterfront property located on Tilghman Island, with a 270-degree water view overlooking both Dogwood Harbor and Harris Creek. Step back in time to experience...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
Welcome to Waterfront Bliss, your ultimate private waterfront retreat nestled in picturesque Tilghman Island, Maryland. This luxurious 4-bedroom, 3-bathroom coastal estate offers unparalleled...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
Located on the Chesapeake Bay side of Tilghman Island, this beautiful two-story, three bedroom cottage is available for rent throughout the year. Our cottages have stunning views of the bay from...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Welcome to your Tilghman Island getaway, a beautifully maintained 3-bedroom cottage located in one of the most convenient areas on the island. This home offers the perfect setting for...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Escape to this cozy 2-bedroom Tilghman Island cottage, just minutes from local restaurants and water access. Enjoy a peaceful Tilghman island getaway for couples, families, or...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
STN-22-40ONE OF OUR MOST SOUGHT AFTER PROPERTIES!MINUTES FROM ST. MICHAELS......Peaceful retreat with breathtaking sunsets located on Tilghman Island.Kayaking, sailing, fishing, are all with in 100...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Escape to Maryland's beautiful Eastern Shore and experience the peaceful charm of Tilghman Island. Whether you're planning a family vacation, couples' getaway, fishing trip, or relaxing...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Talbot County License STRN-23-41Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from the local seafood market or grill what you catch from the private pier. The house...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St....
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Escape to this beautifully designed Tilghman Island retreat, the perfect blend of coastal charm and modern comfort. Ideal for families, couples, and small groups, this pet-friendly getaway...
Created Jul 20, 2026
2 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Escape to The Hootenanny, a charming pet-friendly vintage cottage nestled in the heart of Tilghman Island. Thoughtfully designed and timeless character, this two-bedroom retreat is the...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Tilghman, Maryland
ST-217-FLUWelcome to your dream waterfront getaway just moments away from the charmingtown of St. Michaels. This meticulously designed vacation home is tailored forthe ultimate relaxation and...
Created Jun 15, 2025
4 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Summary:Heart of the Island & Pet Friendly Retreat on Tilghman Island!Step into a thoughtfully curated space where coastal decor meets serene comfort. The open-concept living area is flooded with...
Created Jun 15, 2025
1 Br Private Vacation Home Vacation Rental In Tilghman Island, Maryland
Located on the Chesapeake Bay side of Tilghman Island, our beautiful property is host to several cottages (one, two and three bedroom) that are available for rent throughout the year. The Bayside...
Created Jun 8, 2025
