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Holiday Rentals in Talbot County
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Top Cities in Talbot County

St. Michaels
Our top choices for Talbot County holiday rentals

Station House East: Upscale Loft in the Historic District Cambridge, MD
Station House East: Upscale Loft in the Historic District Cambridge, MDDowntown Cambridge
10.0 out of 10, Exceptional, (7)
The price is €223
includes taxes & fees
27 Jan - 28 Jan 2026

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.6 out of 10, Exceptional, (108)
The price is €139
includes taxes & fees
30 Dec - 31 Dec

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Relax on Kent Island in a 4 Bedroom Home w/Waterview!Stevensville
9.8 out of 10, Exceptional, (42)
The price is €232
includes taxes & fees
5 Jan - 6 Jan 2026

Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach PassesNorth Beach
10.0 out of 10, Exceptional, (17)
The price is €298
includes taxes & fees
27 Jan - 28 Jan 2026

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, RestaurantsNorth Beach
10.0 out of 10, Exceptional, (31)
The price is €345
includes taxes & fees
30 Dec - 31 Dec

Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake BayLusby
9.8 out of 10, Exceptional, (40)
The price is €248
includes taxes & fees
4 Jan - 5 Jan 2026

Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (32)
The price is €240
includes taxes & fees
5 Jan - 6 Jan 2026

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MDPort Republic
9.4 out of 10, Exceptional, (6)
The price is €154
includes taxes & fees
2 Jan - 3 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Talbot County Hotel Reviews

Inn at Perry Cabin
10/10 Excellent
Find out more about Talbot County
Holiday Homes in Talbot County
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