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.

St. Michaels Pet Friendly Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$365 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to St. Michaels are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    6 Matching Rentals in St. MichaelsView all 15 rentals
    Sort by:
    Default
    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Waterview Cottage In St. Michaels!1 / 25
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (11)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 9, 2018
    My family and I spent the week after Christmas in St. Michaels in this amazing historic cottage in the heart of town. We nestled in next to the fire most nights, cooked some...
    Reviewed October 9, 2017
    Everything is exactly as pictured! I love the hardwood floors and enjoyed sitting outside on the patio! As noted in the name, this cottage is centrally located to the shops...
    See all reviews
    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
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 28, 2017
    Very clean, very cute rental! The location could not be better. One block from Talbot St, where all the shops and restaurants are, and one block form the marina. only complaint...
    Reviewed February 22, 2017
    The house is located about a block away from the main street and about a block away from the waterfront. We appreciated that the house was pet-friendly for our dog. The home...
    See all reviews
    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
    Location Information
    St. Michaels, Talbot County NA
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    St. Michaels, Talbot County 21653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best St. Michaels rentals sent straight to your email!
    Get the List
    List your property
    Owner log in