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Vacation Rentals

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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!
8080 Bozman-Neavitt Road
St Michaels, MD 21663
(410) 745-9701
Waterfront Cottages on Harris Cove, a unique waterfront cottage village! Come try our Bed & Boat!
211 N Talbot St
St Michaels, MD 21663
(410) 770-9093
Offering a unique portfolio of waterfront vacation rental homes in St. Michaels, Easton, Oxford, Tilghman Island and Dorchester County. Plan your St. Michaels vacation rental today!
208 Carpenter Street
PO Box 727
St Michaels, MD 21663
(410) 745-2929
The Two Swan Inn is located on St. Michaels' historic harborfront. Our location is superb . . only two short blocks from town center,fabulous restaurants, museums, boat tours and ''specialty shops.
6140 Mariners Court
Tilghman Island, MD 21671
(410) 886-2500
We rent WaveRunners, Jet-Skis, Power Boats, Sailboats, Kayaks, MotorScooters, Bikes, Fishing/Crabbing Gear. Kayak our scenic nature trails. Free training/certification. Just minutes from St. Michaels
6747 Holly Woods Rd
Sherwood, MD 21665
(410) 886-2400
An Eastern Shore hideaway that will delight the most discerning guests. Custom-built waterfront home in a secluded wooded setting with glorious views and deepwater pier.
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. Vacation rentals by the week with in-ground pool and waterfront access for crabbing with 14' rowboats for guest use.
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
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.
9 items found View On Map


Click here for Hot Deals/Specials
Click here to request Visitor’s Guide or more info
Visitor Info Center on the corner of S. Talbot & Mill Street


Click here for Hot Deals/Specials
Click here to request Visitor’s Guide or more info
Visitor Info Center on the corner of S. Talbot & Mill Street


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St. Michaels Business Association, Inc.
P.O. Box 1221, St. Michaels, MD 21663
Call 410-745-0411 or toll-free 800-808-7622 Copyright 2010