Vacation Rentals

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211 N Talbot St
St Michaels, MD 21663
(410) 770-9093
Largest selection of vacation homes in St. Michaels and surrounding areas. Weekly and Weekend vacations, year round. Waterfront homes, private pools and docks, cottages and pet friendly homes.
6140 Mariners Court
Tilghman, MD 21671
(410) 886-2500
Rent WaveRunners/Jet-Skis, Power Boats, Sailboats, Kayaks, Stand-up Paddleboards, Bikes, Fish/Crabbing Gear. Kayak our scenic nature trails. Free training/certification. Just minutes from St. Michaels
300 North Talbot Street
St Michaels, MD 21663
(443) 786-7220
Our inventory of vacation homes is on a par with the luxury and comfort offered in the Hamptons. All our exclusive, prestigious waterfront homes have private pools, docks, and some have tennis courts.
Tilghman Island Realty, Inc. (Booking Agent)
6094 Tilghman Island Road
Tilghman, MD 21671
(410) 886-2400
A custom-built luxury waterfront vacation home in an exceptionally private wooded setting with glorious views and deepwater pier. Top-to-bottom renovation completed in 2016.
208 Carpenter Street
PO Box 727
St Michaels, MD 21663
(410) 745-2929
The Two Swan Inn is located on St. Michaels' historic harbor front. Our location is superb, only two short blocks from town center, fabulous restaurants, museums, boat tours and ''specialty shops.
108 N. Talbot Street
St Michaels, MD 21663
(410) 745-6702
Chesapeake Bay Real Estate Plus - Dawn Lednum Owner/Broker. The Biggest, Little Office in St. Michaels! We ARE your local realtors. Let us show you what's for sale! You're Going to Love It Here!
21606 Chicken Point Road
Tilghman, MD 21671
(410) 886-2643
Waterfront cozy 2 bedroom cottage, screened porch, full kitchen, hot tub, kayak launch, all amenities in the quaint fishing village of Tilghman Island. Free WiFi, gas grill, fish and crab off the doc
6601 Bozman-Neavitt Road
Bozman, MD 21612
(717) 392-4876
Charming cottages and 4 bedroom main house on Broad Creek about 5 miles from town. In-ground pool and waterfront access for crabbing with 14' rowboats for guest use. Available all year.
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