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Vacation rentals in Talbot County

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Top-rated vacation rentals in Talbot County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Tilghman Island Panoramic Views + Pool, Dock
Entire residential home · 8 guests · 8 beds · 4.5 baths
Tilghman Island Panoramic Views + Pool, DockSix acre Tilghman Island estate is perfect blend of nature and luxury. Two hours door-to-door from Baltimore or DC, this is literally the end of the Maryland Eastern Shore "scenic peninsula," with sweeping 270º views of the Chesapeake Bay. Brand new, 40' saltwater pool and hot tub. 110' dock with 3' LMW. Tilghman is one of few remaining watermen's villages on the Bay, and history buffs will love the Waterman's Museum's and historic "W" homes. The island is home to 300+ bird species. ST-475-EAG
St. Michaels-Historic Dist.  Margaret Wells House
SUPERHOST
Entire cottage · 4 guests · 2 beds · 2 baths
St. Michaels-Historic Dist. Margaret Wells HouseThe Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.
The Little Anchor Cottage, St. Michaels, MD
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bath
The Little Anchor Cottage, St. Michaels, MDWelcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

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Other great vacation rentals in Talbot County

SUPERHOST
  1. Entire guesthouse
  2. Cambridge
"Happy Campers" Waterfront Apartment!
$150 per night
SUPERHOST
  1. Entire guesthouse
  2. Stevensville
Waterfront Getaway - View of bay from your bed
$212 per night
SUPERHOST
  1. Entire cottage
  2. Saint Michaels
La Casita on Harris Creek, St. Michaels
$293 per night
SUPERHOST
  1. Entire cottage
  2. Wittman
"Wittman Cottage"
$165 per night
  1. Entire rental unit
  2. Cambridge
Little Slice of Cambridge. Newly listed, 2 bedroom
$99 per night
  1. Private room
  2. Saint Michaels
St. Michaels Harbour Inn - 2 Queen WF Suite
$125 per night
SUPERHOST
  1. Entire rental unit
  2. Stevensville
Boutique by the Bay
$195 per night
  1. Entire cottage
  2. Oxford
Tilghman Cottage I - Cheerful and Charming Oxford
$90 per night
SUPERHOST
  1. Entire cottage
  2. Neavitt
The Middle Point Cottage at Saint Michaels
$214 per night
  1. Entire cottage
  2. Oxford
Tilghman Cottage II
$200 per night
SUPERHOST
  1. Entire cottage
  2. Stevensville
Cottage on the Bay - Kent Island
$350 per night
  1. Entire guesthouse
  2. Cambridge
Small house rental
$165 per night