Oxford Vacation Rentals

Step back in time to the 1600's when you arrive at the charming waterfront village of Oxford, one of the oldest towns in America. A former colonial port with a rich maritime history, the tree-lined streets of Oxford, have maintained their historic charm with original homes and white picket fences. Located near the mouth of the Tred Avon River, Oxford is a major port for Chesapeake Bay yachting and home to several marinas with sailboats coming and going throughout the day.

The historic district of Oxford is a perfect destination for those looking for smaller cottages and a desire to park the car and walk or bike to restaurants and parks.  Larger homes situated outside the town proper offer respite and seclusion within minutes of this quaint nautical town.

Things to Do In Oxford


While Oxford may lack the traditional commercialized vacation activities, there is plenty to explore for those looking for a relaxing and inspiring getaway.  The scenic Morris Street runs through the center of town and is flanked with historic homes and charming cottages.  The quiet village park has some play equipment for little ones as well as picturesque sunsets over the Tred Avon River. The expansive water views provide for the endlessly lazy afternoon of watching sailboats breezy by while the little ones enjoy playing. Morris Street is also home to the Oxford Museum, the Oxford Market and a handful of small shops.  At the end of Morris Street, the Oxford Bellevue Ferry, the oldest privately owned ferry dating from the 1600's, waits to carry you across the river for a quick day trip to St. Michaels, Easton, or Tilghman Island.  You can also enjoy "The Strand" a beach area that also offers amazing views.

Dining in Oxford

Experience bay breezes and some of the best sunsets you will ever see while enjoying some freshly steamed crabs and perhaps a local band strumming along the waterside.  There are two great venues, Doc's Sunset Grille and Capsize, both offering local flavors and a place to dock your boat should you come by water.  History and casual but upscale cuisine blend for a great dining experience at both Pope's Tavern and the Robert Morris Inn and you won't be disappointed by a visit to Latitude 38, located just on the outskirts of town.  The brunch is a local favorite!  Located in another of Oxford's historical buildings is the Scottish Highland Creamery, with over 600 original flavors this is a definite stop-over for ice-cream lovers.

Outdoor Activities in Oxford

Outdoor enthusiasts will find plenty of activity in and around Oxford. Take to the water and rent a kayak, boat or paddleboard at nearby Dockside Boat Rentals. Cyclists will enjoy the flat terrain and can take advantage of the popular cycling route between the three towns of Easton, Oxford, and St Michaels. There are two small beaches, a small sandy area within the village park, perfect for watching the boats and beautiful sunsets across the Chesapeake Bay. Strand Beach is a public beach overlooking the Tred Avon River.

A newcomer to the area is the Oxford Dog park, which is located behind the Community Center and gives your furry friend a place to run and play in a fenced-in area.  Most of our Oxford homes are pet-friendly, so your dog will enjoy this vacation as well!

Children will enjoy the tennis and basketball courts, located in the center of town.  Oxford is a very family friendly community with activities suited to just about everyone.

Eastern Shore Vacation Rentals offers a wide range of Oxford vacation rentals, browse and book these beautiful properties today!