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Holiday Rentals and Villas in St. Michaels, MD

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    Travellers to St. Michaels are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 12
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and... View all property information
    Location Information
    St. Michaels, Talbot County
    1 / 35
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Satellite TV
    • Ocean Views
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Pool, Shoreline, Small Private Beach, Acreage, Lawn, Barbecue, and Nature. Spacious 6000+ square foot home. Up-to-date Gourmet Kitchen. Large and Open Common Spaces. Wall of Glass Overlooking the Chesapeake. 4 Master Suites with Attached Bathrooms and Each with King Bed, Day Bed and Trundle... View all property information
    Location Information
    St. Michaels, Talbot County
    3 of 5 stars 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. It...
    5 of 5 stars 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 "Watermark...
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    1 / 29
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Satellite TV
    • Waterfront
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels.<BR><BR>The house was built around 1840 by Washington Melson, a sailor,... View all property information
    Location Information
    St. Michaels, Talbot County
    5 of 5 stars Reviewed 2 weeks ago
    What a lovely time we had.. Just my dad..now 88, myself 48 and my son 8, and our dog. A lovely home.VERY CLEAN. Just the right size for us! Great washer and dryer, dishwasher...
    5 of 5 stars Reviewed 6 August 2016
    This is a great place to stay if you like looking back in time and having some modern amenties. One side is from1840 (referbished well) the other side newer but built with the...
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    1 / 33
    5 of 5 stars (7) Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Satellite TV
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    St. Michaels, Talbot County
    5 of 5 stars Reviewed 3 September 2015
    So much fun and great memories had in the Harrison House. Location to town and marina...FANTASTIC! We stayed for 11 days! House has so much character and a great level back yard...
    5 of 5 stars Reviewed 27 May 2015
    This house is a totally amazing old home with lots of character. The kitchen is well stocked and there are many bedrooms and bathrooms for a large crowd. We enjoyed sitting...
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Balcony
    • Grill
    • Terrace
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming waterfront 2-story cottage on Oak Creek is just off the Miles River, minutes from the historic village of St. Michaels, spectacular water view with a 75' long, deep water (6") private dock with bench seating. Canoes and kayaks can be launched off the sandy beach in the backyard. Great... View all property information
    Location Information
    St. Michaels, Talbot County
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The home is located in the heart of the estate area of Talbot County. It is within minutes of St. Michaels, Oxford, Cambridge and Easton - yet privacy abounds on your ten acre estate. There is an extensive list of activities to keep everyone busy or just relax on one of the decks or perhaps enjoy... View all property information
    Location Information
    St. Michaels, Talbot County
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Balcony
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round... View all property information
    Location Information
    St. Michaels, Talbot County
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