Mga matutuluyang bakasyunang may daanan papunta sa beach sa 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”.

Away at the Bay: New Home on the Chesapeake Bay!

Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walking distance to a small community beach. Enjoy kayaking, biking, and crabbing on Kent Island right out of your front door. Perfect for multiple families (especially with younger kids) or attending one of the many wedding venues! 15 minutes off the Bay Bridge and easy access to groceries stores, outlet shopping, and restaurants. Come stay with us and enjoy being away at the bay!

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.

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay 100ft away. Water views from most rooms plus treehouse vibes. 4 bedrooms + 4 full bath. Custom luxury upgrades, new appliances. Pull out daybed +2 folding queen mattresses, rustic leather sectional sofas can sleep 4 more (14+total), outdoor grills, covered balconies, hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

Cozy Cottage

Escape to this beautiful cottage overlooking the Chesapeake Bay. Just steps from the beach, this getaway offers water views right from the comfort of the living room. The interior has been remodeled and stylishly furnished, with two bedrooms and one bathroom. This cottage is perfect for couples, small families, or a peaceful solo retreat. Minutes from Downtown Annapolis, the Naval Academy, and other points of interest. NOTE: currently doing yard work; the backyard does not have grass yet

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

JANUARY AND FEBRUARY 2026 WINTER SPECIAL. Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered lower patio & enclosed upper level.

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

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.

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.

Waterfront-View of Bay from your Bed-Steamy Sauna

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.

Chesapeake Houseboat Getaway

Chesapeake Houseboat “Julia's Arc" at the Kentmorr Marina in Stevensville, MD has it all. Great location for Fishing Trips, Wedding Attendees, or anyone who wants to float on a barge with Eastern Shore Nautical Charm. With a private marina beach on the Chesapeake and outdoor activities: sports fishing, biking, golf, sight seeing abound. Welcome aboard for an unforgettable vacation stay.

Punch Point boasts a sandy beach w/ pool and pier

TREMEZZO STAY - Punch Point Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD. If you do not see availability for your dates or are looking to sleep more/less, please visit our other exclusive listings! Chesapeake Mansion (sleeps 12) Ranch at Royal Oak (sleeps 12) Spencer Creek Cabin (sleeps 8)