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Vacation Rentals in St. Michaels, MD and nearby

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    All 15 Rentals in the St. Michaels Area
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    From
    $471
    / Night
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    1 / 22
    5 of 5 stars (1) Excellent
    St. Michaels
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    From
    $628
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    1 / 18
    St. Michaels
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
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    From
    $565
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    1 / 13
    5 of 5 stars (6) Excellent
    St. Michaels
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (6) Make Enquiry
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    $954
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    1 / 38
    St. Michaels
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Boat Available
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    From
    $245
    / Night
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    1 / 23
    5 of 5 stars (2) Excellent
    St. Michaels
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • DVD Player
    • Fireplace
    • Water Views
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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.... View all property information
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    Location Information
    St. Michaels, Talbot County NA
    5 of 5 stars Reviewed 28 May 2015
    I stayed at the Blades house last week and everything was just what we wanted. The location is beyond perfect (in walking distance of everything) and the house had all of the...
    5 of 5 stars Reviewed 18 August 2014
    Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
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    From
    $452
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    1 / 32
    5 of 5 stars (6) Excellent
    St. Michaels
    7 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Internet Access
    • Stereo System
    • Waterfront
    • Fireplace
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 15 June 2015
    My daughter was married in St. Michaels in May so I rented this house and filled it with family. It was a perfect "home base" for all of the activities surrounding the wedding...
    5 of 5 stars Reviewed 4 June 2015
    We loved this house and especially the location! Plenty of room for 11 of our friends! We loved the outside area and being right on the water! Walking distance to so many places...
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    From
    $239
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    1 / 29
    5 of 5 stars (12) Excellent
    St. Michaels
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Fireplace
    • Washer
    • Satellite TV
    • Waterfront
    • Internet Access
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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. The house was built around 1840 by Washington Melson, a sailor,... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 22 August 2014
    The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
    5 of 5 stars Reviewed 20 July 2014
    We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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    From
    $352
    / Night
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    1 / 9
    St. Michaels
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Deck
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    St. Michaels, Talbot County 21662

    The following rentals are within 15 kilometres of St. Michaels, Talbot County, Maryland.

    From
    $220
    / Night
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    1 / 20
    5 of 5 stars (4) Excellent
    Tilghman
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • DVD Player
    • Water Views
    • Satellite TV
    • Washer
    • Air Conditioning
    • Waterfront
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina... View all property information
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    Location Information
    Tilghman, Talbot County 21671
    5 of 5 stars Reviewed 4 June 2015
    This is a delightful place to stay with lots to see and do in the area, from the Maritime Museum in St. Michaels, to Cambridge, to the Ward Museum In Salisbury. We anticipated...
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    $157
    / Night
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    1 / 21
    Tilghman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on... View all property information
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    Location Information
    Tilghman, Talbot County 21671
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    $302
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    1 / 20
    Easton
    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Water Views
    • Satellite TV
    • Dryer
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to... View all property information
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    Location Information
    Easton, Talbot County 21601
    From
    $314
    / Night
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    1 / 17
    Tilghman
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • There Are Tennis...
    • Ocean Views
    • Wi-Fi
    • Water Views
    • Watersports Nearby
    • Satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet... View all property information
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    Location Information
    Tilghman, Talbot County 21671
    From
    $471
    / Night
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    1 / 9
    5 of 5 stars (1) Excellent
    Bozman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Fireplace
    • Stereo System
    • Boat Available
    • Air Conditioning
    • Waterfront
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas... View all property information
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    Location Information
    Bozman, Talbot County 21612
    From
    $835
    / Night
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    1 / 7
    5 of 5 stars (9) Excellent
    Bozman
    4 Bedrooms / 2 Bathrooms / Sleeps 13
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • Internet Access
    • Boat Available
    • Air Conditioning
    • Washer
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large... View all property information
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    Location Information
    Bozman, Talbot County 21612
    5 of 5 stars Reviewed 9 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is a...
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    From
    $314
    / Night
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    1 / 11
    4.5 of 5 stars (2) Very good
    Claiborne
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Internet Access
    • Stereo System
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake... View all property information
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    Location Information
    Claiborne, Talbot County 21663
    4 of 5 stars Reviewed 27 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    5 of 5 stars Reviewed 10 October 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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