- Pet-Friendly Beach Getaway, Relax by the Bay!Annapolis10.0
- Adorable 2-bedroom bungalow near Easton, DentonDenton9.7
- Riverfront Denton Estate on 7 Acres with Fire Pit!Denton
- Rock Hall Retreat with Balcony Near Park and Marina!Rock Hall
- Comfortable Cottage for a Getaway on Maryland's Eastern ShoreRock Hall
- BeachcomberStevensville
- Winchester Creek EstateGrasonville1.0
- Pier Pleasure Retreat- Waterfront & Private Pier
- Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails
- Romantic Getaway in a Country Inn in the Upper Chesapeake Bay, MarylandRock Hall
- 2 Mi to Sandy Point State Park Home with Deck!Annapolis10.0
- Twin Ponds LodgeCentreville
- River Heights Retreat
- Peaceful Queenstown Home with Deck and Grill!Grasonville9.7
- Blake House Historic Estate with Private InnCentreville10.0
- Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!Annapolis9.6
- Elegant Cottage Rental on Maryland's Eastern ShoreRock Hall
- Caribbean Themed Pool Home - 25 min to USNAStevensville
- Charming Room Rental for a Weekend Getaway on Maryland's Eastern ShoreRock Hall
- Captain’s Quarters - unique home on Corsica River!Centreville9.4
- Romantic Cottage Getaway for Two in the Chesapeake Bay in MarylandRock Hall
- Cottage for a Getaway in the Chesapeake Bay Area, MarylandRock Hall
- Hyatt Place Kent Narrows And MarinaGrasonville9.0
- Bayside cottage steps from the harborRock Hall5.0
- Cozy Bed and Breakfast Room for a Weekend Getaway on Maryland's Eastern ShoreRock Hall
- Waterfront Millington Vacation Rental with Hot Tub!
- Pet-Friendly Home on Chester River with Dock!Chestertown
- Countryside Suite for a Lovely Getaway in Maryland's Chesapeake Bay AreaRock Hall
- Carriage House Hideaway In Center of ChestertownChestertown9.8
- Grasonville Home with Private Pool on the WaterGrasonville9.4
- Upscale Cottage Rental for a Weekend Getaway in Maryland's Upper Chesapeake BayRock Hall
- A Shore Thing
- Waterfront Annapolis Home Fire Pit and Fishing PierAnnapolis9.8
- Gorgeous Creek Side Ranch-Style Estate With DockGrasonville
- Charming Cottage Rental for a Getaway in Northeastern MarylandRock Hall
- Spacious Vacation Room for a Romantic Getaway to Northeast MarylandRock Hall
- On-Site Boat Dock Queenstown Home with Pool and Yard!Grasonville
- Walk to Lake and Boat Ramp Central Gem in AnnapolisAnnapolis
- Relaxation Haven on the Shore near Choptank River - Self Catering, a Family n Group FavorGreensboro
- Charming Cottage Rental in the Chesapeake Bay, MarylandRock Hall
