Orlofseignir í Tred Avon River

Cozy 2BR Home near Idlewild Park

"Welcome to your cozy retreat in the heart of Easton, Maryland, a small, charming town nestled on Maryland's Eastern Shore. Step into our recently updated two-bedroom, one-bathroom home, where every detail has been carefully curated to provide you with comfort and style. As you enter, you'll be greeted by a welcoming, open floor plan that effortlessly blends casual living with stylish design. The colors are serene and neutral, creating a peaceful ambiance perfect for relaxation. The fully equipped kitchen beckons to culinary enthusiasts, offering everything you need to whip up delicious meals during your stay. Whether you're brewing your morning coffee or preparing a gourmet dinner, you'll find all the tools at your fingertips. After a day of exploring the quaint streets of Easton or discovering the natural beauty of the Eastern Shore, retreat to the comfort of our quiet neighborhood. Unwind with a good book in the living room, or gather around the dining area for a leisurely meal with loved ones. When it's time to rest, sink into plush bedding in one of the two cozy bedrooms, each thoughtfully appointed for a restful night's sleep. Experience the charm of Easton from the comfort of our stylish home – book your stay today and make memories to last a lifetime."

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

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

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

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

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.

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

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.

Cozy, Family-Friendly Log Cabin-St. Michaels

Escape to our family-owned log cabin on private wooded acreage just 3 miles from historic St. Michaels and 8 miles from Easton. Overlooking a 1-acre freshwater pond, the cabin offers peaceful seclusion with modern comforts, including central heat/air, a fully equipped kitchen, and TVs in every bedroom. Relax on covered and open decks, gather around the fire pit, or enjoy outdoor dining with the grill—all while surrounded by nature. Talbot Co. License #STN-24-27

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

Waterfront Family Retreat - mins from St. Michaels

Dive into luxury with a huge pool, relaxing spa, and outdoor hangout area complete with TV, fire pit, and comfy seating. Inside, cozy up by the fireplace on the massive couch, enjoy Sonos surround sound, and cook in the chef-ready kitchen. Fenced yard with a play area for little ones, breathtaking sunsets, and a private dock for crabbing and fishing—perfect for entertaining, unwinding, and making unforgettable memories with family and friends.