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Talbot County, MD Holiday Rentals, Homes and Villas
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Maryland (MD)
Talbot County, MD Holiday Rentals, Homes and Villas
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Neighbourhood
46 rentals
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*****Waterfront home w/ pool in St. Michaels
33 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!
11 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks
94 reviews
5 bedrooms
4 bathrooms
Sleeps 10
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
84 reviews
7 bedrooms
9 bathrooms
Sleeps 20
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St. Michaels Area Cottage - Walk to Water & Marina
2 bedrooms
2 bathrooms
Sleeps 4
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!
33 reviews
5 bedrooms
3 bathrooms
Sleeps 8
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Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland
93 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing
46 reviews
4 bedrooms
5 bathrooms
Sleeps 8
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Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
44 reviews
3 bedrooms
3 bathrooms
Sleeps 7
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Fully remodel 2 bedroom country cottage.
52 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Beautiful Tidewater home between Easton & ST Michaels!
32 reviews
4 bedrooms
7 bathrooms
Sleeps 8
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Comfy home on beautiful Leadenham Creek. Book now for summer!
31 reviews
5 bedrooms
4 bathrooms
Sleeps 10
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Premier Cottage in St. Michaels- In Town Location!
15 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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St. Michael's Waterfront Vacation Home
39 reviews
5 bedrooms
5 bathrooms
Sleeps 12
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway
25 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Location Location! St Michaels-- In Town Cottage!
24 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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Gorgeous Sunsets and Chesapeake Charm
75 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Waterfront Getaway on the Choptank River
41 reviews
2 bedrooms
1 bathroom
Sleeps 6
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Eastern Shore Getaway Near St. Michaels
69 reviews
1 bedroom
2 bathrooms
Sleeps 2
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton
33 reviews
5 bedrooms
4 bathrooms
Sleeps 10
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Main House at Grandview at Pleasure Point
13 reviews
5 bedrooms
3 bathrooms
Sleeps 13
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town
14 reviews
7 bedrooms
4 bathrooms
Sleeps 9
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Holidays at the Cove - plenty of space to gather while making memories
30 reviews
5 bedrooms
7 bathrooms
Sleeps 10
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Charming 3 Bedroom 3 Bath Beach Front Property
23 reviews
3 bedrooms
3 bathrooms
Sleeps 12
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New Modern Waterfront Farmhouse Built 2018
12 reviews
4 bedrooms
4 bathrooms
Sleeps 10
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Relax in Tilghman Island
18 reviews
4 bedrooms
2 bathrooms
Sleeps 6
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RESTORED WATERFRONT COTTAGE
10 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Sandy Pines: Enjoy Harris Creek w/Pool and Boats
5 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Luxurious Waterfront Kent Island Home 30 miles from Annapolis
23 reviews
4 bedrooms
5 bathrooms
Sleeps 7
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Oxford Waterfront Cottage-Walk to Town, Kayak, Dock, and Bikes
9 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Waterview Cottage In St. Michaels!
5 reviews
2 bedrooms
3 bathrooms
Sleeps 5
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Pot Pie House
2 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX
2 reviews
1 bedroom
1 bathroom
Sleeps 6
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview
3 reviews
5 bedrooms
5 bathrooms
Sleeps 10
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Not to early to think about joining us this Spring and Summer.
3 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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St. Michael's Premier in Town Summer Cottage!
1 review
2 bedrooms
2 bathrooms
Sleeps 4
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Cottage 2 at Grandview Pleasure Point
1 review
2 bedrooms
1 bathroom
Sleeps 6
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Waterfront Property, Kayaks, Private Dock, Near Town
1 review
3 bedrooms
3 bathrooms
Sleeps 6
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
1 review
3 bedrooms
4 bathrooms
Sleeps 6
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Bay Cottage Resort
6 bedrooms
5 bathrooms
Sleeps 12
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St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes
5 bedrooms
4 bathrooms
Sleeps 10
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Cottage 1a at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 4
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Cottage 1b at Grandview Pleasure Point
1 bedroom
1 bathroom
Sleeps 2
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Tranquil Easton Waterfront Property
3 bedrooms
4 bathrooms
Sleeps 6
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6942 Travelers Rest
4 bedrooms
4 bathrooms
Sleeps 10
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Private waterfront estate with pool, convenient to Easton and St. Michaels
5 bedrooms
5 bathrooms
Sleeps 10
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