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Talbot County House Rentals

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    Travellers to Talbot County are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    19 Matching Rentals in Talbot CountyView all 31 rentals
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    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    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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    Halos'Haven Vacation Rental1 / 15
    (3)Very good
    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 11 September 2018
    We stayed at Halos Haven for a girls getaway weekend. Location and property were lovely. Great space for large groups. Having rented homes many times in the past, this...
    Reviewed 13 July 2018
    A group of us stayed at this house for a weekend and it was perfect. The pool was a perfect temperature, the kayaks were easily accessible and the view was amazing. We also...
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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 21647
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    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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    Royal Oak, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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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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    Location Information
    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Bozman, Talbot County 21612
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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 21653
    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
    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 21612
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Main House at Grandview at Pleasure Point1 / 34
    (13)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • 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 21612
    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
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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 21663
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Pot Pie House1 / 12
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2016
    Absolutely lovely stay! The home is spotless and cozy, set in a secluded neighborhood just a short drive away from St. Michaels, so we had our choice of easily getting into town...
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    About this property
    Pot Pie House - Newly Renovated Historic Cottage Located Close to St. Michaels MD Welcome to Pot Pie House! Immerse yourself in Eastern Shore culture in this newly renovated historic cottage located in the quaint waterfront village of Wittman, just minutes from St. Michaels. According to locals,...
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    Location Information
    St. Michaels, Talbot County 21676
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Best sunrise in St. Michaels....Broadview Bay House1 / 24
    (3)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 December 2017
    It's not everyday we find a place that feels immediately comfortable, just like home....but with the best view ever. We loved having the 4 kayaks to head out in the morning to...
    Reviewed 5 December 2017
    We stayed at this terrific house/property for a week this past summer and could not have been happier. The house is spacious, extensively updated, and well-appointed. The...
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    About this property
    Wonderful newly renovated large family home on Harris Creek. With 6 bedrooms and 3 full bathrooms (including master bedroom suite), this house easily sleeps 12. Broad views of the water, 250 foot pier, in ground pool and large 2.5 acre expanse of lawn make this home an amazing retreat. Hang out...
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    Location Information
    St. Michaels, Talbot County 21665
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    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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    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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