Skip to main content
MENU
Toggle navigation
Guest Login
Owner Login
410.770.9093
List Your Property
410.770.9093
List Your Property
Home
Vacation Rentals
All Properties
Properties for Upcoming Events
Search by Community
Search by Type
Need Flexible Dates?
Current Promotions
Current Specials
Plan Your Trip
Frequently Asked Questions
Rental Terms & Conditions
ESVR Rules & Regulations
Rental Guardian Travel Protection
Talbot County Short Term Rentals
Area Guide
Things to Do
Local Events
List Your Property
Vacation Rental Management Services
Owner’s Login
Apply Now
About
About Us
Contact Us
Meet Our Team
Blog
Loading...
Loading...
Guests
2+
4+
6+
8+
10+
12+
14+
Bedrooms
1+
2+
3+
4+
5+
6+
7+
Advanced
Amenities & Options
Boat Slip/dock = Yes
Hot Tub / Jacuzzi = Yes
Pets Allowed = Yes
Pool Type = Private Outdoor Pool
Location = Waterfront
Areas
Areas
Area = Annapolis
Area = Cambridge
Area = Centreville
Area = Chestertown
Area = Easton
Area = Oxford
Area = St. Michaels
Area = Tilghman Island
Search by Property Name
Search by Property Name
22 Fleet Street
Acorn Point
At Tricefields Court
Bay Water Cottage
Bayberry Cove
Belle Aire Landing
Ben Oaks Drive
Blue Gates
Broadwater View
Bushey Heath Farm
Captain's Cove
Carpenter Alley Cottage
Caulk's Cove
Cedar Cove on the Miles
Chesapeake Pines
Clearview
Crabber's Cove
Creek Cottage
Duck Cove
East Street Easy Walk
Emily's Lane
Escape Farm
Graceful View
Heron Point
Holland Point Preserve
Hudson Manor
Indian Fields
Judith's Garden
Lee Haven
Loblolly Cove
Mallard Point Cottage
McKendree Street Mainland
Memory Lane
Mill Creek
Monasterevin
Nantucket on the Chesapeake
Osprey Point
Oxford Beach Cottage
Oxford Oasis
Oyster Cottage
PennyWhistle
Pines at Barrett Cove
Pines at Irish Creek
Pride and Joy
Retreat on Grace Creek
Riverview Retreat
Simplicity Cottage
Sunflower Cottage
Sunrise Cove
Swan's Rest
Sycamore Acres
The Bay House on Easy Lane
The Bird's Nest
The Landing
The Water House
Thornton
Tidal Serenity
Town and Country
Waverly
Willoughby
Windward Cove
New Properties
Search Properties
Homes With Pools
Search Properties
Luxury Properties
Search Properties
Pet-Friendly Homes
Search Properties
Cottages
Search Properties
Multi-Family Homes
Search Properties
Seasonal Rentals
Search Properties
Corporate Retreats
Search Properties
Homes With Docks
Search Properties
Homes With Hot Tubs
Search Properties
