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Holiday Rentals near Skipjack H.M. Krentz

Sailing Charters departing Daily from, St. Michaels, Maryland 21663
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    Travellers to St. Michaels are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 18 Rentals in St. Michaels
    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (11)Very good
    7.6 kilometres from Skipjack H.M. Krentz
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    4.7 kilometres from Skipjack H.M. Krentz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (7)Very good
    7.7 kilometres from Skipjack H.M. Krentz
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    7.7 kilometres from Skipjack H.M. Krentz
    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 9 January 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 9 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...
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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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    St. Michaels, Talbot County
    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
    7.7 kilometres from Skipjack H.M. Krentz
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • 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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    St. Michaels, Talbot County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Waterview Cottage In St. Michaels!1 / 25
    (3)Very good
    7.6 kilometres from Skipjack H.M. Krentz
    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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    Location Information
    St. Michaels, Talbot County
    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
    6.0 kilometres from Skipjack H.M. Krentz
    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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    Location Information
    Neavitt, Talbot County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    7.9 kilometres from Skipjack H.M. Krentz
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Grill
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    6.8 kilometres from Skipjack H.M. Krentz
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces,...
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    Location Information
    Bozman, Talbot County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5.2 kilometres from Skipjack H.M. Krentz
    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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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sandy Pines:  Enjoy Harris Creek w/Pool and Boats1 / 22
    (5)Excellent
    7.0 kilometres from Skipjack H.M. Krentz
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2018
    Took the whole family for a big birthday weekend and the house was perfect. Owner Brad is very responsive and booking was a breeze. The house was spacious, clean, and even has a...
    Reviewed 26 January 2017
    We had a group of women here to celebrate a birthday. We wanted to hang out, relax, eat, drink, and sleep and were pleased with our choice to stay at Sandy Pines. The view is...
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    About this property
    Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and...
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    Location Information
    St. Michaels, Talbot County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Main House at Grandview at Pleasure Point1 / 34
    (13)Excellent
    6.8 kilometres from Skipjack H.M. Krentz
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This is our 4th year coming to the St. Michaels area for our anniversary. This was our first time staying at the grand view. We were in cottage 1B. PerfectLocation, quiet...
    Reviewed 20 September 2018
    What a terrific week we had . Young and old enjoyed our stay. Perfect weather and plenty of crabs made our visit special. Grandview is the perfect family vacation spot.
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    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,...
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    Location Information
    Bozman, Talbot County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 18
    (2)Excellent
    7.5 kilometres from Skipjack H.M. Krentz
    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 8 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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    6.5 kilometres from Skipjack H.M. Krentz
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambiance of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Location Information
    Bozman, Talbot County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6.5 kilometres from Skipjack H.M. Krentz
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Location Information
    Bozman, Talbot County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    7.7 kilometres from Skipjack H.M. Krentz
    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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    7.3 kilometres from Skipjack H.M. Krentz
    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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    6.1 kilometres from Skipjack H.M. Krentz
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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