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Kirkland Hall Manor
| An outstanding example of Georgian architecture, from sweeping lawns to the majestic pillared porch and sunny spacious waterfront More» |
| Bedrooms: 6 |
Pet Friendly: Call |
| Sleeps: 10 |
Fireplace: Yes |
| Pool: Yes |
Dock: Yes |
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Leggacy on the Miles
High on the banks of the upper Miles River, where the ferryboats once docked, located on a point surrounded by spectacular water views More» |
| Bedrooms: 5 |
Pet Friendly: No |
| Sleeps: 10 |
Fireplace: Yes |
| Pool: Yes |
Dock: Yes |
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San Sano
| A combination of 16th century Palladian and Jeffersonian architecture, this 134 acre waterfront estate is just minutes by water to the village of St Michaels.
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| Bedrooms: 5 |
Pet Friendly: No |
| Sleeps: 10 |
Fireplace:Yes |
| Pool: Yes |
Dock: Yes |
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Sycamore Llanding
| One of Maryland's oldest (c.1659) and most picturesque estates on the Miles River, Sycamore Llanding has been updated, yet retains all of its original character More» |
| Bedrooms: 5 |
Pet Friendly: No |
| Sleeps: 10 |
Fireplace:Yes |
| Pool: No |
Dock: No |
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Duxbury
| Surrounded by tall, shady trees and wonderfully landscaped gardens, this "Lady of the Bay" home, offers privacy and comfort More» |
| Bedrooms: 5 |
Pet Friendly: Yes |
| Sleeps: 8 |
Fireplace: No |
| Pool: Yes |
Dock: Yes |
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The Manor at Long Haul
| Built on a point overlooking the Miles River and Long Haul Creek, it is hard to imagine that you are minutes from historic St Michaels More» |
| Bedrooms: 5 |
Pet Friendly: Yes |
| Sleeps: 8 |
Fireplace: Yes |
| Pool: Yes |
Dock: Yes |
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Leeds Creek
| This colonial (c1800) is one of the most private and prestigious estates on the Eastern Shore. 35 acres, private cove, boat house, large pool More» |
| Bedrooms: 5 |
Pet Friendly: Yes |
| Sleeps: 10 |
Fireplace: Yes |
| Pool: Yes |
Dock: Yes |
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Millwood Manor
| Set in the midst of 100 acres, Millwood is the classic Eastern Shore "gentleman's farm", with westerly views of Trippe Creek More» |
| Bedrooms: 5 |
Pet Friendly: Yes |
| Sleeps: 10 |
Fireplace: Yes |
| Pool: Yes |
Dock: Yes |
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Wimbledon on Wye
| Among estates and farms on the Wye River is Wimbledon on Wye. Entering through antique iron gates, down a the tree lined lane, passing tennis courts More» |
| Bedrooms: 5 |
Pet Friendly: No |
| Sleeps: 10 |
Fireplace: No |
| Pool: Yes |
Dock: Yes |
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The Captain Harrison House
| The Captain Harrison House is one of the oldest homes on the island. With three floors, private dock, and personal island More» |
| Bedrooms: 5 |
Pet Friendly: No |
| Sleeps: 10 |
Fireplace: No |
| Pool: No |
Dock: Yes |
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Provence
A traditional country home, nestled amongst 100 year old trees
on magnificent grounds overlooking the Miles river, this secluded estate
is ideally located More» |
| Bedrooms: 4 |
Pet Friendly: No |
| Sleeps: 8 |
Fireplace: Yes |
| Pool: Yes |
Dock: Yes |
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The Beach House
| In the town of Oxford proper, is a most wondrous surprise – a house with its own private beach! This darling 4 bedroom home reminds one of Nantucket More» |
| Bedrooms: 4 |
Pet Friendly: Call |
| Sleeps: 8 |
Fireplace: Yes |
| Pool: Yes |
Dock:Yes |
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Miles Away
| Located between Easton and St Michaels on Glebe Creek, this is an easy ride to by road or up the Miles River to St Michaels by boat.More» |
| Bedrooms: 4 |
Pet Friendly: No |
| Sleeps: 8 |
Fireplace: Yes |
| Pool: Yes |
Dock:Yes |
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Cranford on Miles
| Get away
and relax at Cranford on the Miles, a piece of true Eastern shore elegance dating
back to 1840.Tucked away on over 3 park-like acres More» |
| Bedrooms: 3.5 |
Pet Friendly: Call |
| Sleeps: 8 |
Fireplace: Yes |
| Pool: Yes |
Dock:Yes |
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The Shore
| Wake up to the sun rising over the water, with the calls of osprey, blue heron and bald eagles and wander down to your own private dock to enjoy the soft morning light while sipping your coffee. More» |
| Bedrooms: 3 |
Pet Friendly: No |
| Sleeps: 6 |
Fireplace:Yes |
| Pool: No |
Dock:Yes |
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Casa de Suenos
| HGTV 2002 Dream House
of the year, Casa de Suenos is the only vacation home in Talbot County that is actually on the Chesapeake Bay More» |
| Bedrooms: 3 |
Pet Friendly: No |
| Sleeps: 6 |
Fireplace: Yes |
| Pool: Yes |
Dock:No |
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Pine Grove
| Nestled in a small waterman's village is a secret hide-away known as Pine
Grove Cottage. Full of twists and turns, this cottage
is amazingly large More» |
| Bedrooms: 3 |
Pet Friendly: No |
| Sleeps: 6 |
Fireplace: Yes |
| Pool: Yes |
Dock:Yes |
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Tilghman Island Manor
| Step back in time to Tilghman Island Manor, a perfect blend of Victorian Charm and modern amenties and is ready for your whole family! Bring the kids More» |
| Bedrooms: 3 |
Pet Friendly: Yes |
| Sleeps: 5 |
Fireplace: No |
| Pool: No |
Dock:No |
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Prairie Wind
| Designed by Washington architect Suman Sorg and Associates and landscaped by James van Sweden, this property is a master piece More» |
| Bedrooms: 2 |
Pet Friendly: No |
| Sleeps: 4 |
Fireplace: No |
| Pool:Yes |
Dock:No |
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Distinctive Waterfront Estate Rentals