A rare to find home on the Eastern Shore that can sleep up to 22! Great for multiple family vacationing, this property has been thought out to give each family...

Treat yourself to a fun filled vacation. New, large contemporary home that overlooks Barren Island and Opossum Island in Hoopers Island.

Wide water views with great sunsets, Sunset Bay is perfect for those larger family vacations where you need the extra space and activities.

Fishing Cove is a fully-furnished eight-bedroom six-bath waterfront family-friendly house tucked away in a lush pine forest. Our waterfront vacation home is on a...

Chesapeake Bay Waterfront Vacation Rental-Cambridge Neck Region. Welcome Home to Sunset Bay! Enjoy your vacation in this beautiful holiday house.

A charming 3BR cottage just outside of Cambridge, Cedar Point is a self contained recreation destination for a small family or group.

We are strictly a family retreat, no exceptions. ADA compliant elevator for all your families needs. This home is nestled away in a private waterfront community.

Here is a unique opportunity to stay in a charming, historic home in the Neck District, Maryland's most beautiful, unspoiled areas.

Bayberry Cove is the perfect Chesapeake Bay private retreat for a family vacation or a group of friends and kids to get away from it all.

Experience the amenities of the Chesapeake Hyatt with the comforts of home! Enjoy our 2 bedroom 2 bath condominium with waterfront views of the Choptank River and...

Located on the Lodgecliffe Canal in historic Cambridge, Maryland, Heron’s View Vacation Home is just a quick paddle from the Choptank River and the banks of...

This property is the perfect waterfront location for your next family getaway. There are five acres with many large trees that provide a great deal of privacy.

Brick rancher nestled on a 23-acre nature hideaway. Large deck attached to a huge screened porch overlooking in-ground pool and private cove.

Enjoy a week with your friends and family at a charming 1895 Victorian house in the historic district of Cambridge - in Dorchester County, on Maryland's scenic...

Come to Ransome's Chesapeake Retreats 'RCR', a private, 250-acre, waterfront estate with one mile of shoreline on the magnificent Chesapeake Bay of Eastern Shore,...

This beautiful waterfront home is the perfect balance of traditional, immaculate grand home and casual peace and quiet. 'Windswept' is located high on a bluff...

Family retreat perfection! This fabulous, new, luxury home is on 500 feet of private Chesapeake waterfront, near Cambridge, and close to Easton, & St Michaels. It...

Looking for a vacation rental that feels like a new resort? With acres of secluded waterfront, this luxury property is just 10 minutes from Cambridge, & close to...