A stone church with a pointed steeple and arched windows.

Holiday Homes in Talbot County

Compare and save

  • 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

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Talbot County holiday homes

A waterfront property with a wooden dock leading to a large house.

1. Modern Chesapeake Waterfront - Heated Pool - Dock

Modern Chesapeake Waterfront - Heated Pool - Dock
2.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
Modern Chesapeake Waterfront - Heated Pool - Dock
A spacious living area with a large gray sectional sofa, a dining table with chairs, and a kitchen with gray cabinets and a stainless steel range hood.

2. Peaceful Pet Friendly Chesapeake Escape 4 Bedroom Home

Peaceful Pet Friendly Chesapeake Escape 4 Bedroom Home
3.0 star property
Prince Frederick
Peaceful Pet Friendly Chesapeake Escape 4 Bedroom Home
A two-story residential house with a garage, a front lawn, and a satellite dish.

3. Kent Island Getaway with Fire Pit Near Annapolis

Kent Island Getaway with Fire Pit Near Annapolis
3.0 star property
Stevensville
Kent Island Getaway with Fire Pit Near Annapolis
A family of three at a round metal table with a plate of food, seated outside a house with a corrugated metal wall.

4. Downtown Flat Walk to Dining Shops Sleeps 4

Downtown Flat Walk to Dining Shops Sleeps 4
2.0 star property
Downtown St. Michaels
Downtown Flat Walk to Dining Shops Sleeps 4
A wooden dock extending into calm water with boats docked in the background and a forested shoreline.

5. Boho Waterfront Getaway 5 Bedroom Retreat

Boho Waterfront Getaway 5 Bedroom Retreat
2.0 star property
Lexington Park
Boho Waterfront Getaway 5 Bedroom Retreat
A kitchen with white cabinets, a black countertop, and a sign that reads "Solomons Island".

6. Solomons Island 6BR Family Getaway

Solomons Island 6BR Family Getaway
2.0 star property
Solomons
Solomons Island 6BR Family Getaway
A swimming pool surrounded by lush greenery and stone steps leading to the pool area.

7. Private 5BD Country Escape With Spa Pool Fire Pit

Private 5BD Country Escape With Spa Pool Fire Pit
2.0 star property
Port Republic
Private 5BD Country Escape With Spa Pool Fire Pit
A spacious living room with a large sliding glass door leading to a deck, a fireplace, and a dining area with a view of greenery.

8. Waterfront Kent Island Retreat 5BR Sleeps 12 Near Weddings Annapolis

Waterfront Kent Island Retreat 5BR Sleeps 12 Near Weddings Annapolis
2.0 star property
Stevensville
Waterfront Kent Island Retreat 5BR Sleeps 12 Near Weddings Annapolis
A spacious living room with a fireplace, comfortable seating, and large windows.

9. Creekside Haven With Dock Scenic Views

Creekside Haven With Dock Scenic Views
2.0 star property
Hollywood
Creekside Haven With Dock Scenic Views
A wooden interior with a staircase, a sofa, and a ceiling fan.

10. Lusby Beach House -3 BD 2 BA Steps to the Sand

Lusby Beach House -3 BD 2 BA Steps to the Sand
2.0 star property
Lusby
Lusby Beach House -3 BD 2 BA Steps to the Sand
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."
Yvette 1-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Find out more about Talbot County

Talbot County Holiday Homes information

Number of reviews
Accommodation
10 Holiday Homes
Lowest Price
Highest Price