We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Apartments and Cottages in St. Michaels, MD

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 8 Rentals in St. Michaels
    loading...
    Don't let other travelers get your favorite St. Michaels vacation rental. You're so close to securing your perfect getaway. Book today.
    Sort by
    From
    $375
    Per Night
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $500
    Per Night
    View Details
    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
    Overview Make Inquiry
    From
    $450
    Per Night
    View Details
    1 / 13
    5 of 5 stars (6) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Reviews (6) Make Inquiry
    From
    $759
    Per Night
    View Details
    1 / 38
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Make Inquiry
    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
    Make Inquiry
    Location Information
    St. Michaels, Talbot County 21663
    From
    $150
    Per Night
    View Details
    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Inquiry
    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
    Make Inquiry
    Location Information
    St. Michaels, Talbot County NA
    5 of 5 stars Reviewed May 28, 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 August 18, 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!
    See all reviews
    From
    $290
    Per Night
    View Details
    1 / 32
    5 of 5 stars (6) Excellent
    7 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Reviews (6) Make Inquiry
    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
    Make Inquiry
    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed June 15, 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 June 4, 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...
    See all reviews
    From
    $150
    Per Night
    View Details
    1 / 29
    5 of 5 stars (13) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (13) Make Inquiry
    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
    Make Inquiry
    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed July 15, 2015
    Access to lots of restaurants - enjoyed the whole experience! Excellent restaurants,within walking distance of where we were staying, We would HIGHLY recommend this...
    5 of 5 stars Reviewed August 22, 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...
    See all reviews
    From
    $280
    Per Night
    View Details
    1 / 9
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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
    Make Inquiry
    Location Information
    St. Michaels, Talbot County 21662
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing