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Pet Friendly Holiday Rentals in St. Michaels

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    $415 Average
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    Travellers to St. Michaels are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    6 Matching Rentals in St. MichaelsView all 15 rentals
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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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    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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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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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 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...
    Reviewed 15 September 2017
    The cottage was in the perfect location to walk around town, try different restaurants, or enjoy the harbor. The house was cozy and had everything we needed!!
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    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,...
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    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    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...
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    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 9
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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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