Photo by JensTrvlBug

Holiday Rentals in Talbot County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Top Cities in Talbot County

Holiday RentalsHoliday Rentals

St. Michaels

St. Michaels

Our top choices for Talbot County holiday rentals

Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7)
The price is €223
includes taxes & fees
27 Jan - 28 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is €139
includes taxes & fees
30 Dec - 31 Dec
First Floor Studio Apartment in Historic Chestertown
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is €232
includes taxes & fees
5 Jan - 6 Jan 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 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!"
United States
Jennifer B.
The price is €298
includes taxes & fees
27 Jan - 28 Jan 2026
Walk to Beach! King Bed & Free Beach Passes
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is €345
includes taxes & fees
30 Dec - 31 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Sun-loungers, beach towels
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (40)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is €248
includes taxes & fees
4 Jan - 5 Jan 2026
Soul Oasis - home on the Chesapeake Bay
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
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. "
United States
Pamela
The price is €240
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Coastal/Country Home w/3 Acres & Sauna!
Fridge, microwave, stovetop, coffee/tea maker
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, MD

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Port Republic
9.4 out of 10, Exceptional, (6)
"I was traveling for work and this was a perfect spot to stay for me. "
United States
Tyler B.
The price is €154
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is €232
includes taxes & fees
28 Dec - 29 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is €254
includes taxes & fees
5 Jan - 6 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Interior
Upscale Condo in Annapolis

Upscale Condo in Annapolis

Upscale Condo in Annapolis
Historic District
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is €456
includes taxes & fees
22 Jan - 23 Jan 2026
Upscale Condo in Annapolis
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is €307
includes taxes & fees
12 Jan - 13 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is €307
includes taxes & fees
5 Jan - 6 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €386
includes taxes & fees
27 Jan - 28 Jan 2026
Waterfront Oasis of Annapolis Star
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is €302
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
North Beach
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is €241
includes taxes & fees
28 Dec - 29 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (6)
"Very clean and very convenient location for our trip. "
United States
Greg S.
Charming Pet-Friendly Stay - Near Bay & Beaches.
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.2 out of 10, Wonderful, (37)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
Large 2 bedroom house with private parking in a nice neighborhood
Terrace/patio
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (7)
"Enjoyed the stay"
United States
Kedra B.
The price is €318
includes taxes & fees
30 Dec - 31 Dec
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Sun-loungers
Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is €276
includes taxes & fees
28 Dec - 29 Dec
Cottage Located on the Patuxent River!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Talbot County Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Fantastic - loved our stay!"
Emily 1-night trip
Posted 3 days ago
Inn at Perry Cabin

Find out more about Talbot County

Holiday Homes in Talbot County

Search for holiday homes in Talbot County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Talbot County using one of the methods below: 

  • View our selection of featured holiday homes in Talbot County
  • Use the map to find apartments and other holiday rentals in the Talbot County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Talbot County while they last

Look no further and take a look at our great range of rental properties in Talbot County!