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St. Michaels Holiday Homes

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    Travellers to St. Michaels are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 14 Rentals in St. Michaels
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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (21)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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    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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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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    Amenities & Details
    • Satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Great place to stay in a beautiful town!
    Reviewed 13 October 2016
    We were in St Michaels for our son's wedding with all our family. The house easily accommodated the 8 of us, with a variety of living spaces so we could visit in small groups...
    Feel like you are part of history
    Reviewed 10 October 2016
    The owners of the Harrison House have taken great pains to make you feel part of history. St Michaels is all about the period around the War of 1812, and this house dates from...
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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 21663
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 9
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    Pot Pie House1 / 12
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Cozy get-away for a girls weekend
    Reviewed 14 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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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sandy Pines: Enjoy Harris Creek w/Pool and Boats1 / 22
    (4)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)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    This Is The Place to Relax Comfortably
    Reviewed 27 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...
    Fantastic family house rental
    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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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds1 / 38
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Waterview Cottage In St. Michaels!1 / 25
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Charming, historic house, but might not be good for everyone.
    Reviewed 17 June 2017
    The cottage is full of colonial charm, and the owner was helpful. We really appreciated being able to bring our dog. However, we had envisioned being able to leave her on the...
    Wonderful house in a wonderful town!
    Reviewed 29 May 2017
    We stayed at the John Bruff house recently during a return trip to St Michaels for the wine fest weekend. I can't say enough about this vacation rental, it's comfortable, full...
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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 21663
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Historic Waterfront Property with Wi-Fi and Dock1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Halos'Haven Vacation Rental1 / 14
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    McDaniel, St. Michaels 21647
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Comfortable, Spacious & Fun! 6 Acres Pool & Shore1 / 35
    (3)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Beach is greatly overstated
    Reviewed 5 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...
    perfectly relaxing weekend
    Reviewed 28 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
    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...
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    Location Information
    St. Michaels, Talbot County 21676
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    BACK STREET RETREAT1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Balcony
    • Grill
    • Terrace
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 6
    (2)Excellent
    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
    Kid friendly
    Smoking allowed
    Very nice place
    Reviewed 9 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...
    Perfect place in a quiet residential neighborhood, but within walking distance to town
    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 21663
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    St. Michael's Premier in Town Summer Cottage!1 / 7
    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
    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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