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Vacation Rentals nearby Tilghman Island

Tilghman Island Road, St. Michaels, Maryland
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    Travellers to St. Michaels are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 44 Rentals in St. Michaels
    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    4.9 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Waterview Cottage In St. Michaels!1 / 25
    (6)Excellent
    5.0 kilometres from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview1 / 36
    (2)Very good
    4.8 kilometres from Tilghman Island
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    St. Michael's Premier in Town Summer Cottage now with private pool!1 / 4
    (2)Excellent
    5.4 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
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    • DVD Player
    • Washer
    • Housekeeping Included
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2021
    Wonderful experience. House was perfect and owner responsive. I would highly recommend for anyone who is looking for a getaway to St. Michael's.
    Reviewed June 30, 2019
    My three sisters and I stayed here for two nights in June and loved this cottage. Even before arriving, I had a good feeling because Carol, the owner, is very responsive and...
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    About this property
    Harbor Hideaway's in town location is a rare find and now we have a private pool! HH's in town location is just steps away from everything that St. Michael's has to offer, including the public access to the water! A charming story and a half cottage that has been completely renovated with amenities...
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Classic Eastern Shore Waterfront Manor House - ST-9361 / 30
    (10)Excellent
    2.1 kilometres from Tilghman Island
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    7.5 kilometres from Tilghman Island
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    4.8 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    6.1 kilometres from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    7.5 kilometres from Tilghman Island
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
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    • Patio
    • Waterfront
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    Pet friendly
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    About this property
    TRUE IN-TOWN SAINT MICHAELS 5.5 ACRE WATERFRONT w/POOL!!!! Talbot County License Number: ST-251-LYT If you do not see availability for your dates or are looking to sleep 12 please visit our 2 additional exclusive listings!! Chesapeake Mansion or Ranch at Royal Oak This 3000+ square foot home...
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    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!1 / 24
    (80)Very good
    5.0 kilometres from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    5.0 kilometres from Tilghman Island
    6 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 9
    4.8 kilometres from Tilghman Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    5.5 kilometres from Tilghman Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.2 kilometres from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    McDaniel, St. Michaels
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Dollhouse in Central Historic St Michaels1 / 11
    (5)Excellent
    4.8 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    The Water House | Over The River And Through The Woods!1 / 30
    (7)Excellent
    6.0 kilometres from Tilghman Island
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
    4.2 kilometres from Tilghman Island
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Luxury Waterfront with pool and deep water dock, minutes from St Michaels.1 / 30
    (5)Excellent
    2.4 kilometres from Tilghman Island
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    McDaniel, St. Michaels
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    4.9 kilometres from Tilghman Island
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    4.9 kilometres from Tilghman Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels1 / 15
    (4)Excellent
    4.2 kilometres from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.1 kilometres from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch1 / 22
    (17)Excellent
    4.9 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    5.2 kilometres from Tilghman Island
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bathroom, Sleeps 2
    5.6 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR1 / 30
    (6)Excellent
    3.8 kilometres from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
    • Parking
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    Pet friendly
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    St. Michaels, Talbot County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4.1 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    4.9 kilometres from Tilghman Island
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels1 / 24
    (82)Excellent
    5.0 kilometres from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    5.4 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Skiing: Property Is In A Ski Resort
    • DVD Player
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4.8 kilometres from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3.1 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    Talbot County rental license ST-644-LYT This is our newest listing and it is a stunner! If you do not see availability or are looking for something else please visit our additional exclusive listings. Chesapeake Mansion (sleeps 12) Spencer Creek Cabin (sleeps 8) The space Over the years we have had...
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    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!1 / 30
    (4)Excellent
    4.1 kilometres from Tilghman Island
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    1.7 kilometres from Tilghman Island
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    McDaniel, St. Michaels
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    1.6 kilometres from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    McDaniel, St. Michaels
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3.9 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Ship's Cove Inn and Resort at St. Michaels allows you to chart your own course for the perfect family vacation. If it’s a quiet family getaway that you seek, explore the lovely shops, restaurants or wineries in town or discover the magic of the Miles river in kayaks available for use during your...
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    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town1 / 23
    (106)Excellent
    5.0 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels1 / 15
    (5)Very good
    4.9 kilometres from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Riverview Retreat - Charming Waterfront Cottage in St Michaels!1 / 30
    (5)Excellent
    5.8 kilometres from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    6.2 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.7 kilometres from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Walk to Everything House1 / 14
    (7)Excellent
    4.8 kilometres from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!1 / 23
    (3)Excellent
    3.8 kilometres from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront Estate.  **WALK TO ST. MICHAELS!**1 / 30
    (3)Excellent
    3.9 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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