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St. Michaels Holiday Rentals

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    Travellers to St. Michaels are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 29
    5 of 5 bubbles (21) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 21
    5 of 5 bubbles (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 28
    4.5 of 5 bubbles (11) Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Private Garden
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The Cottage is just steps to the harbor and to museums, shops, restaurants, parks etc. The house is a 2 bedroom 2 full bathroom house with plenty of living space and a large screened porch facing a large... View all property information
    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 bubbles Reviewed 1 week ago
    From my first communications with the property owner all the way to the last day of my rental, I was absolutely impressed! This was for a rental reservation made at the eleventh...
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    1 / 22
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • 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 21612
    5 of 5 bubbles Reviewed 26 January 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...
    5 of 5 bubbles Reviewed 13 January 2017
    We stayed with another family (4 adults 3 teenagers) over memorial day weekend and could not have been happier. The house is spacious and well appointed - we spent a lot of time...
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    1 / 12
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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,... View all property information
    Location Information
    St. Michaels, Talbot County 21676
    5 of 5 bubbles Reviewed 13 June 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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    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Waterfront
    • Balcony
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    St. Michaels, Talbot County 21653
    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 21663
    1 / 35
    4.5 of 5 bubbles (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 21676
    3 of 5 bubbles 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 bubbles 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 / 14
    McDaniel
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool house with bathroom, boat dock... View all property information
    Location Information
    McDaniel, St. Michaels 21647
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    1 / 23
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Private Garden
    • Parking
    • Satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    St. Michaels, Talbot County 21663
    1 / 38
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
    • Private Outdoor...
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A St. Michaels 3.5-acre waterfront vacation rental property with 500' shoreline, private pier, deep-water boat slips, dinghy dock, waterside pool, fire pit, and sundeck. We offer the warmest hospitality and the finest comfort. Walk to St. Michaels, MD attractions - shops, restaurants, brewery,... View all property information
    Location Information
    St. Michaels, Talbot County 21663
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Private Garden
    • Satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    St. Michaels, Talbot County 21663