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Holiday Rentals near Tilghman Island

Tilghman Island Road, St. Michaels, Maryland
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    Travellers to St. Michaels are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 11 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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    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (11)Very good
    3.0 miles 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
    3.1 miles 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
    (14)Very good
    3.1 miles from Tilghman Island
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 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...
    Reviewed 5 August 2019
    This beautiful home is right in the middle of the historic St. Michaels harbor. The water and the benches on Muskrat Park are basically right in your front yard. The place is...
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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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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 9
    Waterview Cottage In St. Michaels!1 / 25
    (5)Excellent
    3.1 miles from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 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...
    Reviewed 28 March 2019
    We had a wonderful stay at the John Bruff House. The house was very comfortable and decorated beautifully. The property has magnificent views of the harbor and park, and is a...
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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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    Location Information
    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
    (3)Very good
    3.0 miles from Tilghman Island
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 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 27 October 2015
    It was a long weekend, so packed our bikes up on Saturday rather fighting traffic on Friday evening. I guess it worked because our trip was fast and smooth. With the...
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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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    Location Information
    Wittman, Talbot County
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 18
    (2)Excellent
    3.4 miles from Tilghman Island
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    Very beautifully decorated place very clean and well taken care of on a very quiet street just a block from the water and about a fifteen minute walk to the hart of st michaels...
    Reviewed 4 July 2017
    The location was perfect - about a 10 minute walk to the central part of St. Michael's. If you prefer to drive, it will only take you about 2 minutes. The owner was helpful...
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    About this property
    Near the water, near the town. Steps to shopping, winery, brewery and more. Enjoy the former renowned painters studio remade into a loft for sleeping, chilling out. You're close to everything at Long Lane Lodge - no need to drive! Enjoy grilling out or building a firepit. St. Michaels has it all....
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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    St. Michael's Premier in Town Summer Cottage!1 / 7
    (1)Excellent
    3.4 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 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! 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 that will help ensure a great...
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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!1 / 48
    (30)Excellent
    4.6 miles from Tilghman Island
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    *****Waterfront home w/ pool in St. Michaels1 / 17
    (31)Very good
    3.9 miles from Tilghman Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.4 miles from Tilghman Island
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Internet Access
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay Cottage 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 stay. For...
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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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