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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 November dates now. Secure your vacation rental today, and have the perfect trip.
    All 38 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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    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (11)Very good
    4.9 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (15)Excellent
    5.0 kilometres from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (15)Very good
    5.0 kilometres from Tilghman Island
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Washer
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    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2021
    Perfect location to enjoy St. Michaels. The home is perfectly situated at the water's edge and across from Muskrat Park. A quick walk to Foxy's Harbor Grill for a cocktail and...
    Reviewed November 11, 2019
    For our annual fall getaway, my friends and I selected St. Michaels and we could not have been happier with our choice. The town is very charming and walkable with a number of...
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    About this property
    The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and...
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    St. Michaels, Talbot County
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 9
    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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    • Private Garden
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    Pet friendly
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    Reviewed June 26, 2021
    Great location with view of the water and boats and Muskrat Park. Location allowed us to walk to nearby shops and restaurants. It was also great to bring our dog, not really a...
    Reviewed October 30, 2019
    My wife and I just got back from a wonderful few days at a beautifully restored historic cottage in St MichaelsCozy, comfortable with incredible water view Watched the...
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    About this property
    The fully restored historic John Bruff House, located on the Town park, has magnificent St. Michaels harbor and Miles River water views. The house is 2 bedroom, 3 bathroom cottage with plenty of living space and a rear screened porch. It is a short walk from all museums, parks, restaurants,...
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    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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    • DVD Player
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    • Ocean Views
    • Private Outdoor Pool (Heated)
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    • Waterfront
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    Suitability
    Pet friendly
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    Smoking allowed
    Reviewed July 4, 2016
    My family was looking for a vacation house that would meet the needs of the entire family. One of the reasons we picked this place was the picture and description of the beach...
    Reviewed September 21, 2015
    I loved staying here! It was such a wonderful weekend full of family and friends. I stayed once over the winter - and it was absolutely lovely then, but summer was even better...
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    About this property
    TALBOT COUNTY SHORT-TERM RENTAL LICENSE: ST-895-REH 2019 10 Person Maximum ***Watermark At a Glance (More Rate Specials Below Description): Heated Pool - season depends on weather. Currently open as of: 10/15. Thanksgiving Week Special Week of November 24-December 1: Book 5 nights, get 2...
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    Wittman, Talbot County
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    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
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    • 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
    Cottage downtown on a quiet street1 / 18
    (59)Excellent
    4.9 kilometres from Tilghman Island
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
    TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT *HEATED POOL*1 / 48
    (50)Excellent
    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
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    Beautiful Waterfront Home w/ Pool In St. Michaels1 / 34
    (46)Very good
    6.1 kilometres from Tilghman Island
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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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)
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    • 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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    Pet friendly
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    Smoking allowed
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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!1 / 25
    (101)Very good
    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
    5.5 kilometres from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Dollhouse in Central Historic St Michaels1 / 10
    (18)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 - Unique 3600-SqFt Home Near St. Michaels!1 / 35
    (6)Excellent
    6.0 kilometres from Tilghman Island
    5 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 8
    4.0 kilometres from Tilghman Island
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Waterfront with pool and deep water dock, minutes from St Michaels.1 / 49
    (15)Excellent
    2.4 kilometres from Tilghman Island
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    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
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    Private+Cozy /3br+3ba /1 mile to Historic Downtown Saint Michaels1 / 15
    (4)Excellent
    4.1 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
    2.7 kilometres from Tilghman Island
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    McDaniel, St. Michaels
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch1 / 21
    (118)Excellent
    4.9 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
    ST MICHAELS- Private Waterfront Home, Dock, Huge Deck&Heated 19’Swim Spa, 2 MBR1 / 34
    (22)Excellent
    3.8 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
    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
    Delightful Close to town1 / 18
    (15)Excellent
    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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    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
    Charming 1930's Cottage including wide dock with 7 foot depth1 / 35
    (6)Excellent
    4.6 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
    Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town1 / 49
    (71)Excellent
    3.4 kilometres from Tilghman Island
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Captain's Cove - Fantastic Family Compound Just 1/2 Mile to Historic District!1 / 29
    (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
    NEW LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL1 / 61
    (1)Excellent
    2.1 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
    Mallard Point Cottage - Relaxing Waterfront Home, Kayaks, Bikes, Pet-Friendly!1 / 32
    (18)Very good
    2.1 kilometres from Tilghman Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    McDaniel, St. Michaels
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3.9 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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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
    (105)Excellent
    5.0 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
    Riverview Retreat - Charming Waterfront Cottage in St Michaels!1 / 30
    (12)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
    Walk to Everything House1 / 13
    (32)Excellent
    4.8 kilometres from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    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
    (14)Excellent
    3.8 kilometres from Tilghman Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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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 / 42
    (3)Excellent
    3.9 kilometres from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Patio
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    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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