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Talbot County Pet Friendly Holiday Rentals

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    Travellers to Talbot County are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in Talbot CountyView all 31 rentals
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 115
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    This house is the perfect place to stay! You are truly a block from everything. The large screened in back porch was enjoyed day and night!
    Reviewed 30 May 2017
    We celebrated my parents 65th anniversary. The house was close to everything so walking was easy. The house is charming, very well laid out, spotless and perfectly in keeping...
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    About this property
    The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The Cottage is just steps to the harbor and to museums, shops, restaurants, parks etc. The house is a 2 bedroom 2 full bathroom house with plenty of living space and a large screened porch facing a large...
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    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 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 22 February 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...
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    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....
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    Location Information
    St. Michaels, Talbot County NA
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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 16 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 28 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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    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    St. Michaels Waterfront Home W/Dock for 2 boats1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    VERY nice place and owner was excellent. Place building is old must has been well maintained. It is very clean and exceeded all our needs. Owner are excellent people!!
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    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring...
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    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Waterfront Room Rentals 1 with Private Beach1 / 34
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Dimitri was very kind and helpful. We throughly enjoyed our stay. The view of the Choptank was beautiful.
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    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
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    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
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    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Comfortable, Spacious & Fun! 6 Acres Pool & Shore1 / 36
    (3)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    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...
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    Location Information
    Wittman, Talbot County 21676
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
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    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • Grill
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Ingleton! Relax by the pool. Fish or crab or picnic at the end of the pier. Do all three. Go biking. Go hiking. Go boating. Visit historic St. Michaels, Easton and Oxford. Watch the sunset from the Adirondack chairs at the water's edge. Eat. Shop. Play golf. Play yard games. Play board...
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    Location Information
    Royal Oak, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4+ acres on Shipshead Creek off of St. Michaels road. Fully furnished (2 king and 4 twin beds), heated pool, deep water dock, tennis court,and pet friendly. Boat, Jet Ski, Paddle Board, Kayak, Canoe, and Bike rentals can be arranged-Inquire if interested The Space Pet Friendly waterfront...
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    Easton, Talbot County 21601
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique apartment sleeps 5 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill...
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    Wye Mills, Talbot County 21679
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 'Land of Pleasant Living' awaits your arrival at Blue Bird Cottage, a 2-bedroom, 2-bathroom Neavitt vacation rental house! Numerous amenities and spectacular peninsula location within walking distance to the water and marina provide up to 4 guests with a serene Maryland getaway. Venture to St....
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    Location Information
    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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