Holiday rentals with beach access in Talbot County

Little Slice of Cambridge. 2 bedroom, pet friendly

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Cottage #1 Lighthouse First Cottage down driveway

OPEN March 25th until October 31st each year. No 1 is First cottage down drive has a full Kitchen, dining table, queen size bed in one open room. Full size Futon, Please call Jaimie upon arrival. Check in 3pm Check out 11am promptly please. Sorry No pets allowed! Bring: bed linens, Towel set, Coffee, filters and condiments for standard pot, bottle waters we are on a well safe to cook with. Boats are separate rentals 16’ , 9hp motor full day $250. 14’ Ft Boat rental with motor 9hp $225 full day

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

Sailor's Cottage - Private Waterfront

Sailor's Cottage lets you get away from it all within walking distance of the charming and historic town of Oxford. This idyllic retreat on 29 acres is the perfect private hideaway for family and friends to enjoy the best of Eastern Shore living. The craftsman-built home is inviting and inspiring. Relax with your morning coffee on the screened-in porch, have cocktails on the dock, or take a paddle on protected Boone Creek. Longer stays are encouraged to take advantage of all there is to do.

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Panoramic water views

Tilghman Island Point of View. Our Island is perfectly situated on the Maryland crab and oyster trail. Step back in time to a slower lifestyle and observe the waterman’s way of life. Enjoy our two-bedroom coastal cottage and Island attractions. Enjoy the bird’s eye view of the local waterman in and out of the harbor seeking the days catch. Walk or kayak the shoreline. Take a stroll or ride a bike to Island attractions including all restaurants and shops. Arrive by boat or car.

Relaxing Retreat on the Hudson

Escape to this stunningly renovated 5-bed, 2-bath waterfront retreat on Hudson Creek in Cambridge, MD. Perfect for small-large groups. Relax in the giant living room, cook in the gourmet kitchen, dock your boat at the pier, charge your EV at the garage, and enjoy the serene water views. 20 min from town - peaceful seclusion. The perfect balance of comfort and style for families, friends, or a memorable getaway. Fishing, Crabbing, Hunting, Writing, WFH, Yoga. Pet-friendly.

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

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.