Holiday Rentals in Talbot County
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Top Cities in Talbot County

St. Michaels
Our top choices for Talbot County holiday rentals

Condo in Downtown Cambridge
Station House East: Upscale Loft in the Historic District Cambridge, MD10.0 out of 10, Exceptional, (7)
The price is €223
includes taxes & fees
27 Jan - 28 Jan 2026

Apartment in Chestertown
First Floor Studio Apartment in Historic Chestertown9.6 out of 10, Exceptional, (108)
The price is €139
includes taxes & fees
29 Dec - 30 Dec

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

Holiday Home in North Beach
Walk to Beach! King Bed & Free Beach Passes10.0 out of 10, Exceptional, (17)
The price is €280
includes taxes & fees
11 Jan - 12 Jan 2026

Holiday Home in North Beach
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants10.0 out of 10, Exceptional, (31)
The price is €345
includes taxes & fees
30 Dec - 31 Dec

Cottage in Lusby
Soul Oasis - home on the Chesapeake Bay9.8 out of 10, Exceptional, (40)
The price is €237
includes taxes & fees
19 Jan - 20 Jan 2026

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

Apartment in Port Republic
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD9.4 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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