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St. Michaels House Rentals

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    Travelers to St. Michaels are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    11 Matching Rentals in St. MichaelsView all 15 rentals
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    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (11)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Halos'Haven Vacation Rental1 / 15
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 28, 2017
    Very clean, very cute rental! The location could not be better. One block from Talbot St, where all the shops and restaurants are, and one block form the marina. only complaint...
    Reviewed February 22, 2017
    The house is located about a block away from the main street and about a block away from the waterfront. We appreciated that the house was pet-friendly for our dog. The home...
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    About this property
    The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor....
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    Location Information
    St. Michaels, Talbot County NA
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Waterfront
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed...
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    Location Information
    St. Michaels, Talbot County 21653
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Yard
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 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 July 4, 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 21663
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Pot Pie House1 / 12
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2016
    Absolutely lovely stay! The home is spotless and cozy, set in a secluded neighborhood just a short drive away from St. Michaels, so we had our choice of easily getting into town...
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    About this property
    Pot Pie House - Newly Renovated Historic Cottage Located Close to St. Michaels MD Welcome to Pot Pie House! Immerse yourself in Eastern Shore culture in this newly renovated historic cottage located in the quaint waterfront village of Wittman, just minutes from St. Michaels. According to locals,...
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    Location Information
    St. Michaels, Talbot County 21676
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sandy Pines:  Enjoy Harris Creek w/Pool and Boats1 / 22
    (5)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 Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2018
    Took the whole family for a big birthday weekend and the house was perfect. Owner Brad is very responsive and booking was a breeze. The house was spacious, clean, and even has a...
    Reviewed January 26, 2017
    We had a group of women here to celebrate a birthday. We wanted to hang out, relax, eat, drink, and sleep and were pleased with our choice to stay at Sandy Pines. The view is...
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    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...
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    Location Information
    St. Michaels, Talbot County 21612
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Best sunrise in St. Michaels....Broadview Bay House1 / 24
    (3)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 6, 2017
    It's not everyday we find a place that feels immediately comfortable, just like home....but with the best view ever. We loved having the 4 kayaks to head out in the morning to...
    Reviewed December 5, 2017
    We stayed at this terrific house/property for a week this past summer and could not have been happier. The house is spacious, extensively updated, and well-appointed. The...
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    About this property
    Wonderful newly renovated large family home on Harris Creek. With 6 bedrooms and 3 full bathrooms (including master bedroom suite), this house easily sleeps 12. Broad views of the water, 250 foot pier, in ground pool and large 2.5 acre expanse of lawn make this home an amazing retreat. Hang out...
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    Location Information
    St. Michaels, Talbot County 21665
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Yard
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 2,000 sq foot fenced in spacious home is the guest quarters for Halo's Haven Horse Rescue in gorgeous historic downtown St. Michaels. 1.25 green acres with fenced in backyard located on a quite street. Located just under a mile to the parks, shops, harbor, restaurants and more...
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    Location Information
    St. Michaels, Talbot County 21663
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    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 21663
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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