Vacation rentals in Oxford

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

Bring the whole family to my spacious house. 3 bathrooms for everyone to get ready. 2 king beds and 2 queen beds across 4 bedrooms. Huge living room, kitchen, and dinning room. Enjoy a sun room and fenced in back yard. Fresh eggs from backyard chickens. Merry Maids regularly cleans the bathrooms and kitchen. The basement, garage, and shed are for storage, and are not part of the rental. While quiet just outside of the city, there maybe some highway noise or farm animal noise. Large driveway

Historic Home in Heart of Oxford, MD

Stay in a historic home built by the railroad when it came to town in 1880 (look for Pennsylvania Railroad memorabilia throughout the house!). Hardwood floors and fireplace with a yard on a quiet street, but in the heart of the historic bay town of Oxford, MD — half a block to the town market, coffee and ice cream, bookstore, and gift stores, and a block to the water on both sides of the house (enjoy beautiful sunrises & sunsets on the water!). Listed on the Natl. Registry of Historic Places.

Arcadia Shores On The Cove

Welcome to our renovated home nestled between Easton and St. Michaels. Situated along the serene Miles River waterfront, this spacious 4 bed & 4 bath retreat offers breathtaking views from every exterior angle. Inside you will find two king suites, a fabulously equipped gourmet kitchen, and a large dining room perfect for entertaining. With a cozy family room, and a large living room that has a queen pull-out and a full bath that can be used as a 5th bedroom. Come, relax and unwind. STRN-25-8

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Luxurious waterfront home - Cèilidh

Beautiful luxury waterfront home in historic downtown Oxford. A rare find with 2 piers, 50+ feet of waterfront and a huge lawn leading to the water! Walk to everything in town! From the large family room and screened porch, unwind and relax as you watch the boats come and go. This 2-story house comfortably accommodates up to 8 guests. With plush beds, ample hang out spaces, workspaces, and a high-end kitchen, it's a luxurious, restful place.

Charming cottage, FP, 1 blk water, historic area

A peaceful oasis near the water in the center of Cambridge. Tucked away at the end of a cul-de-sac with historic connections, this private, charming antique-filled cottage is steps away from the river. Enjoy three comfortable bedrooms all with en-suite bathrooms, and 2 living areas w/ fireplace and view of the Choptank River, with plenty of room for family and friends to entertain. Close to all amenities, Gerry Boyle Park and the waterfront.

Pride and Joy of Oxford | an ESVR property

Tucked away in the quaint, historic town of Oxford, Pride and Joy is a terrific spot for those looking to step back in time when you could walk to the corner store for milk and ice cream, meander up the street to the local produce stand, or simply sit on the front porch and sip a lemonade while enjoying the scenery. The old fashioned charm and white picket fence are a warm welcome to visitors who want to slow it down a bit.

Combsberry – Private Waterfront Estate

Escape to Combsberry — a 1730 waterfront estate surrounded by golden fall foliage and crisp Chesapeake Bay breezes. Perfect for family gatherings, couples’ retreats, or pet-friendly escapes, this 5BR property blends historic charm with modern comfort. Enjoy a pool, gourmet kitchen, and 30 acres of private shoreline near St. Michaels, Easton and Downtown Oxford. Talbot County Licensure: STRN-25-43