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Vacation Rentals near Tilghman Island

Tilghman Island Road, St. Michaels, Maryland
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    Travelers to St. Michaels are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 12 Rentals in St. Michaels
    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (5)Excellent
    3.0 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (11)Very good
    3.1 miles from Tilghman Island
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Halos'Haven Vacation Rental1 / 15
    (3)Very good
    2.1 miles from Tilghman Island
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Waterview Cottage In St. Michaels!1 / 25
    (3)Very good
    3.1 miles from Tilghman Island
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Yard
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 16, 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 May 28, 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Location Location! St Michaels-- In Town Cottage!1 / 54
    (24)Excellent
    3.1 miles from Tilghman Island
    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 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...
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (13)Excellent
    3.1 miles from Tilghman Island
    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 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...
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Comfortable, Spacious & Fun! 6 Acres Pool & Shore1 / 36
    (3)Very good
    2.9 miles from Tilghman Island
    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 July 4, 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 October 27, 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
    Cabin - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds1 / 38
    (1)Average
    2.4 miles from Tilghman Island
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2017
    We rented Bay Cottage for two weeks and were looking forward to the six bedroomhouse and large waterfront property with pool and dock on the MIles River. We arrived to find a...
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    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,...
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    Location Information
    St. Michaels, Talbot County
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 18
    (2)Excellent
    3.4 miles from Tilghman Island
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Private Yard
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2017
    Very beautifully decorated place very clean and well taken care of on a very quiet street just a block from the water and about a fifteen minute walk to the hart of st michaels...
    Reviewed July 4, 2017
    The location was perfect - about a 10 minute walk to the central part of St. Michael's. If you prefer to drive, it will only take you about 2 minutes. The owner was helpful...
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    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....
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    Location Information
    St. Michaels, Talbot County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2.5 miles from Tilghman Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Yard
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 2,000 sq foot fenced in spacious home is the guest quarters for Halo's Haven Horse Rescue in gorgeous historic downtown St. Michaels. 1.25 green acres with fenced in backyard located on a quite street. Located just under a mile to the parks, shops, harbor, restaurants and more...
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    Location Information
    St. Michaels, Talbot County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.3 miles from Tilghman Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have 7 Cottages to choose from that are located on the Harris Creek, Rates fluctuate week day to weekend, and of course seasonal as well. and we are a waterfront property, we have 6 cottage's supplied with Full Kitchen, all utensils, Linen, Bath towels, and stove and refrigerator full size. 1...
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    Location Information
    St. Michaels, Talbot County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3.4 miles from Tilghman Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbor Hideaway's in town location is a rare find! HH's in town location is just steps away from everything that St. Michael's has to offer, including the public access to the water! A charming story and a half cottage that has been completely renovated with amenities that will help ensure a great...
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    Location Information
    St. Michaels, Talbot County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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