Eastern Shore Vacation Rentals

Experience Maryland’s Eastern Shore!

Our hand-selected portfolio of Eastern Shore, MD, vacation rentals includes properties ranging from quaint historic cottages, waterfront vacation homes or estate luxury properties offering the very best of Eastern Shore living. Our pet-friendly rentals cater to the whole family so there’s no need to leave your furry friends behind! Our warm, friendly and knowledgeable staff adds an extra special personalized touch to your dream vacation and our effortless search and booking process ensures an unrivaled Chesapeake Bay vacation experience!

New Rentals

Banyan Cottage - Eastern Shore Vacation Rental — Banyan Cottage

Quailsar Farm - Eastern Shore Vacation Rental — Quailsar Farm

Red Barn Farm - Eastern Shore Vacation Rental — Red Barn Farm

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Featured Rentals

Bay Breeze - Eastern Shore Vacation Rental — Bay Breeze

The Cove at Cambridge - Eastern Shore Vacation Rental — The Cove at Cambridge

The Water House - Eastern Shore Vacation Rental — The Water House

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Search by Popular Amenities

Dock on Tred Avon River in Easton, Maryland — Homes with Docks

Hot tub overlooking Tred Avon River in Easton, Maryland — Homes with Hot Tubs

Dog sticking its head out the car windo — Pet Friendly Homes

Eastern Shore Vacation Rental with a pool — Homes with Pools

Adirondack chairs overlooking Tred Avon River in Easton, Maryland — Waterfront Homes

Pool Table in the Game Room — Homes with Game Room

Search by Popular Amenities

This is the nicest, most elegant and most comfortable house we’ve stayed in for all our years of vacationing on the eastern shore. We’re delighted with our stay.

Michael E.Crew’s Quarters

Beautiful house with so many amenities! We used the kayaks, paddle boards, grill and crab traps. A very quiet area on the bay. Easy drive to Easton and St. Michaels. The jellyfish kept us from swimming in the bay, but everything else was amazing. Would definitely recommend.

Michelle J.Seventh Haven

We loved the house and property. This was our first trip to the area and loved being in a wooded area on a secluded bay. The pool was a hit and kayaking brought us closer to nature. We even had a bald eagle make a nightly appearance.

Charlie K.Magnolia Cove

This home is lovely. We loved our vacation here. The kitchen is so well stocked. The home is meticulous. Loved the bedroom arrangement. Really loved all the seating on the first floor. The screened porch was great. Loved the privacy of the location.

Fran K.Emily’s Lane

Couldn’t love this home enough! comfy beds, great porches (LOVE the screened in back porch) and beautiful views. My favorite thing was walking down to the dock and enjoying my morning coffee. Super close to Tilghman Island and downtown St Michaels with fun restaurants, shops, and breweries. Will absolutely come back! Thank you for the amazing stay!

Alexandra Y.Sailor Joe’s

Eastern Shore Vacation Rentals

Experience Maryland’s Eastern Shore!

New Rentals

Banyan Cottage

Quailsar Farm

Red Barn Farm

Featured Rentals

Bay Breeze

The Cove at Cambridge

The Water House

Search by Popular Amenities

Homes with Docks

Homes with Hot Tubs

Pet Friendly Homes

Homes with Pools

Waterfront Homes

Homes with Game Room

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