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  • Vacation Rentals

    Accommodation Types:
    Accommodation Amenities:
    Results Found: 8 View On Map new search
    Captain's Watch Vacation Cottage
    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
    21606 Chicken Point Road
    Tilghman, MD 21671
    Accepts less than full week's stay Hot Tub/Whirlpool Major Credit Cards Pets Allowed in Lodging Family-friendly WiFi
    Tilghman Island Marina & Rentals
    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
    6140 Mariners Court
    Tilghman, MD 21671
    Eastern Shore Vacation Rentals
    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.
    211 N Talbot St
    St Michaels, MD 21663
    Accepts less than full week's stay Boat/Motors Rental Handicap Accessible Hot Tub/Whirlpool Laundry Facilities Major Credit Cards Outdoor Pool Pets Allowed in Lodging
    Chesapeake Bay Real Estate -Plus LLC-
    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!
    108 N. Talbot Street
    St Michaels, MD 21663
    Tidewater Vacations - Waterfront Rental Homes
    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.
    300 North Talbot Street
    St Michaels, MD 21663
    Boat/Motors Rental Hot Tub/Whirlpool Outdoor Pool Pets Allowed in Lodging Tennis Family-friendly WiFi Bikes
    Overlook on Dun's Cove
    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.
    Tilghman Island Realty, Inc. (Booking Agent)
    6094 Tilghman Island Road
    Tilghman, MD 21671
    Accepts less than full week's stay Laundry Facilities Family-friendly WiFi
    Pot Pie House Vacation Rental
    Historic 3-Bedroom Cottage situated in a small, secluded neighborhood off Harris Creek.Fully equipped kitchen & outdoor grills. Boat slip, bikes and kayaks available. Fall in love with shore living!
    22583 Pot Pie Road
    Whitman, MD 21678
    Accepts less than full week's stay Major Credit Cards Pets Allowed in Lodging Family-friendly Bikes
    Grandview Cottages
    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.
    6601 Bozman-Neavitt Road
    Bozman, MD 21612

  • Before You Visit:

  • St. Michaels, Tilghman and the Bay Hundred area have a wide range of lodging options to suit every taste and budget. Find the perfect place to fit your needs here.

  • Nothing says Chesapeake Bay like a steaming pile of locally caught Maryland blue crabs, and our restaurants are serving the Chesapeake Bay's bounty, from steamed crabs and crab cakes to sweet soft shell clams and fresh rockfish.  Find the perfect restaurant here.

  • St. Michaels offers shopping galore, with an eclectic range of shops, including jewelry, clothing and home decor, galleries and more!   Stop by one of the many tasting rooms, offering specialty foods and locally made libations. Find our unique shops here.

  • Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors!  Find your boating options here.

  • Special thanks to William Wilhelm Photography, the Town of St. Michaels and the Chesapeake Bay Maritime Museum for the use of their photos.

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