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Holiday Homes near Gatsby's Collection

1007 S Talbot St, St. Michaels, Maryland 21663-2633
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    Travellers to St. Michaels are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 15 Rentals in St. Michaels
    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (13)Excellent
    1.4 kilometres from Gatsby's Collection
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    1.4 kilometres from Gatsby's Collection
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    4.4 kilometres from Gatsby's Collection
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Halos'Haven Vacation Rental1 / 15
    (1)Excellent
    7.5 kilometres from Gatsby's Collection
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2017
    Stayed this weekend with 10 friends and loved every minute of it. The land and house are gorgeous! I love the town of st Michaels but the house was so amazing we never...
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    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...
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    McDaniel, St. Michaels
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (11)Very good
    1.3 kilometres from Gatsby's Collection
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • 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 11 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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    St. Michaels, Talbot County
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 9
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    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (5)Excellent
    1.4 kilometres from Gatsby's Collection
    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 6 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 31 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    6.3 kilometres from Gatsby's Collection
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shipwright Cottage is a fully-renovated 2 bedroom, 1 1/2 bath house that is a perfect getaway for couples or small families. Upstairs features two sleeping areas - a bedroom with two extra long twin beds that can be combined to make a king and an open, loft-style bedroom with a queen bed and...
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    Wittman, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 18
    (2)Excellent
    1.0 kilometres from Gatsby's Collection
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 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 4 July 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3.3 kilometres from Gatsby's Collection
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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...
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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4.8 kilometres from Gatsby's Collection
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.7 kilometres from Gatsby's Collection
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • 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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    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterview Cottage In St. Michaels!1 / 25
    (3)Very good
    1.3 kilometres from Gatsby's Collection
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    7.8 kilometres from Gatsby's Collection
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds1 / 38
    (1)Average
    2.7 kilometres from Gatsby's Collection
    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 18 August 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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    0.9 kilometres from Gatsby's Collection
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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