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)
"Amazing and neat and very private "
Alexander M.
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)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
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)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
Jennifer B.
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)
"Perfect place to spend quality time with our three adult children and their significant others. "
Malarkey F.
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)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
Samuel W.
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)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
Pamela
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)
"I was traveling for work and this was a perfect spot to stay for me. "
Tyler B.
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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