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Holiday Rentals in St. Michaels

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    ₹ 24,225 Average
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    ₹ 0₹ 64,000+
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    Travellers to St. Michaels are booking May dates now. Secure your holiday home today, and have the perfect trip.
    All 16 Rentals in St. Michaels
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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (23)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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    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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    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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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    This house is the perfect place to stay! You are truly a block from everything. The large screened in back porch was enjoyed day and night!
    Reviewed 30 May 2017
    We celebrated my parents 65th anniversary. The house was close to everything so walking was easy. The house is charming, very well laid out, spotless and perfectly in keeping...
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    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...
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    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • 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 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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    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)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 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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    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 Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    Halos'Haven Vacation Rental1 / 15
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2017
    Stayed this weekend with 10 friends and loved every minute of it. The land and house are gorgeous! I love the town of st Michaels but the house was so amazing we never...
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    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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    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
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds1 / 38
    (1)Average
    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
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    We rented Bay Cottage for two weeks and were looking forward to the six bedroomhouse and large waterfront property with pool and dock on the MIles River. We arrived to find a...
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    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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    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 1 week ago
    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 1 week ago
    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
    Holiday Rental House - 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 Garden
    • 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have 7 Cottages to choose from that are located on the Harris Creek, Rates fluctuate week day to weekend, and of course seasonal as well. and we are a waterfront property, we have 6 cottage's supplied with Full Kitchen, all utensils, Linen, Bath towels, and stove and refrigerator full size. 1...
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    St. Michaels, Talbot County 21663
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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