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Vacation Rentals near Tilghman Island

Tilghman Island Road, St. Michaels, Maryland
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    Travelers to St. Michaels are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 46 Rentals in St. Michaels
    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    3.1 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Waterview Cottage In St. Michaels!1 / 25
    (6)Excellent
    3.1 miles 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
    3.0 miles 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
    3.4 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Great
    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.
    sweet Cottage In a quiet and convenient location
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Classic Eastern Shore Waterfront Manor House - ST-9361 / 30
    (10)Excellent
    1.3 miles from Tilghman Island
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    *Heated Pool* TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT1 / 30
    (50)Excellent
    4.6 miles from Tilghman Island
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Stay in the HEART of Saint Michaels!1 / 14
    3.0 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Waterfront Home w/ Pool In St. Michaels1 / 30
    (46)Very good
    3.8 miles from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    TRUE ST MICHAELS 6 ACRE WATERFRONT1 / 39
    4.6 miles from Tilghman Island
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
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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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!1 / 24
    (80)Very good
    3.1 miles from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!1 / 25
    (101)Very good
    3.1 miles from Tilghman Island
    6 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Skiing: Property Is In A Ski Resort
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    St. Michaels, Talbot County
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 9
    Modern Studio in heart of town, walk everywhere!1 / 21
    3.0 miles 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
    Harbor View Suite1 / 11
    3.4 miles 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
    Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!1 / 30
    1.3 miles from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    McDaniel, St. Michaels
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Dollhouse in Central Historic St Michaels1 / 11
    (18)Excellent
    2.9 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    The Water House | Over The River And Through The Woods!1 / 30
    (7)Excellent
    3.7 miles from Tilghman Island
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    St. Michaels, Talbot County
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 9
    Crew's Quarters of St. Michaels1 / 30
    2.6 miles from Tilghman Island
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Luxury Waterfront with pool and deep water dock, minutes from St Michaels.1 / 30
    (15)Excellent
    1.4 miles from Tilghman Island
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    McDaniel, St. Michaels
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Book 3 nights in July/August 4 night is free!1 / 30
    3.0 miles 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
    Luxurious studio in heart of historic St Michaels!1 / 22
    3.0 miles 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
    2.6 miles from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Grace Cottage, Saint Michaels Walk to everything!1 / 22
    3.1 miles from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Eastern Shore Vacation Home on the Water!1 / 38
    (4)Excellent
    1.6 miles from Tilghman Island
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    McDaniel, St. Michaels
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch1 / 22
    (118)Excellent
    3.0 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Fabulous in town luxury studio1 / 22
    3.2 miles from Tilghman Island
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Fairview Estate | One Of A Kind!1 / 30
    3.5 miles from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR1 / 30
    (22)Excellent
    2.3 miles from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    St. Michaels, Talbot County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Red Barn Farm of St. Michaels1 / 30
    2.5 miles from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels1 / 24
    (82)Excellent
    3.1 miles from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Modern Studio in heart of town.1 / 16
    3.0 miles from Tilghman Island
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Condo/Apartment - 1 Bathroom, Sleeps 2
    St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!1 / 23
    (59)Excellent
    3.3 miles 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Delightful Close to town1 / 18
    (15)Excellent
    2.9 miles from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    RANCH AT ROYAL OAK- Exclusive waterfront pool pier1 / 41
    1.9 miles from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!1 / 30
    (4)Excellent
    2.5 miles from Tilghman Island
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    St. Michaels, Talbot County
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL1 / 30
    1.0 miles from Tilghman Island
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    McDaniel, St. Michaels
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!1 / 30
    (18)Very good
    1.3 miles from Tilghman Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    McDaniel, St. Michaels
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    The Kipsy, A fabulous St Michaels Waterfront1 / 29
    1.0 miles from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    McDaniel, St. Michaels
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Ship's Cove Inn and Resort in St. Michaels, MD1 / 38
    2.4 miles from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town1 / 23
    (106)Excellent
    3.1 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels1 / 15
    (8)Excellent
    3.0 miles from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Riverview Retreat - Charming Waterfront Cottage in St Michaels!1 / 30
    (12)Excellent
    3.6 miles from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Reserve the Nauti-Hideaway in St Michaels today!1 / 18
    3.8 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Seasonal Rental: Artisan designed 3 bedroom home.1 / 13
    3.5 miles from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Walk to Everything House1 / 13
    (32)Excellent
    3.0 miles from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!1 / 23
    (14)Excellent
    2.3 miles from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront Estate. **WALK TO ST. MICHAELS!**1 / 30
    (3)Excellent
    2.4 miles from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    St. Michaels, Talbot County
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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