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.

Holiday Rentals and Homes 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.
dd/mm/yyyy dd/mm/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
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €405 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to St. Michaels are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 21
    5 of 5 bubbles (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 29
    5 of 5 bubbles (20) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 22
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 28
    4.5 of 5 bubbles (11) Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 bubbles 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 or...
    5 of 5 bubbles 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...
    See all reviews
    1 / 38
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • 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 / 35
    4.5 of 5 bubbles (3) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    1 / 14
    McDaniel
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • 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
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The home is located in the heart of the estate area of Talbot County. It is within minutes of St. Michaels, Oxford, Cambridge and Easton - yet privacy abounds on your ten acre estate. There is an extensive list of activities to keep everyone busy or just relax on one of the decks or perhaps enjoy... View all property information
    Location Information
    St. Michaels, Talbot County 21673
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Waterfront
    • Balcony
    • Air Conditioning
    Suitability
    • 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 / 12
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • 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 / 6
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    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