Vacation Rentals

Vacations on the Eastern Shore leave you with memories to last a lifetime. From a quaint cottage to a waterfront estate Chesapeake Bay Real Estate Plus will turn your vacation dreams into reality. Our property managers will help you choose the best property for your vacation needs. They will personally book your stay and be available to assist you throughout your vacation. Our properties are first class and offer an array of amenities.

When you arrive at one of our properties you will enter a sparkling clean home. Beds will be made and fresh towels will be at your disposal. Each home comes with its own welcome book of information that acquaints you with the home and Bay Hundred area.

So, whether it is a three night jaunt, a month-long adventure or anywhere in between, Chesapeake Bay Real Estate Plus is here to make it happen.

Sunset Cottage, Tilghman Island MD

Sleeps: 6

Bedrooms: 3

Bathrooms: 3

Minimum Stay: 3 nights

Upon arrival, you realize this is the Eastern Shore Experience you have been looking for….A gated garden welcomes you to this charming Bayside cottage that has been completed renovated to take advantage of the broad views of the Chesapeake Bay. You can sip your coffee in the gated garden with the flora and the fauna, catch your crab dinner from the private pier, then enjoy your freshly steamed crabs on an outdoor picnic table watching a spectacular sunset. There is no better way to spend a summer evening! The screen porch is the perfect setting to sip a beverage and watch the Osprey catch their dinner. On colder days, there is a cozy seating area in the great room that also affords you the beautiful views. You can even start a fire in the unique, European style, glass enclosed fireplace in the great room. The dining areas in the home are many from the waterside cafe table, screen porch dining area, breakfast bar or formal dining area, you choose what suits your mood! Preparing ameal or steaming your crabs in the well-equipped kitchen is a great experience. There is also a gas grill available for you to use. When’s it’s time to leave this little paradise you can stroll to the village of Tilghman, explore the harbor of a true working waterman’s village, visit the museum or Nautical bookstore, grab ice cream at the Country Store or visit a local restaurant. Many destinations are just a short stroll away. The property is perfect for a romantic getaway or family vacation. All bedrooms are located on the main level for easy access. Stay for a week or just a long weekend – your visit to the land of pleasant living will be memorable and enjoyable.

Crosswinds, TILGHMAN ISLAND MD

Sleeps: 12

Bedrooms: 6

Bathrooms: 5.5

Minimum Stay: 3 nights

Welcome to Crosswinds! This newly renovated waterfront home is being offered for vacation rentals for the first time! We welcome you to start a tradition for your annual getaway where you will create memories of a lifetime!

Located on Harris Creek on Tilghman Island, the views will take your breath away and transport you to a land of tranquility and relaxation. The kids will be ecstatic to swim in the indoor, heated pool and play foosball in the game room come rain or shine. Not to mention, crabbing, fishing, kayaking, and exploring "The Island" which are only a few of the treasured pastimes of the area.

Historic St Michaels is a short drive away and offers exceptional dining opportunities, a gorgeous harbor, and one of a kind shops along Main Street.

A private dock where you can catch crabs or fish, kayaks, a wrap-around deck for barbecues, 6 bedrooms, 5.5 bathrooms, an indoor pool with jacuzzi; all secluded on a point surrounded by water....what more could you ask for! Come enjoy eastern shore hospitality at Crosswinds.

Happy Place,Tilghman Island MD

Sleeps: 6

Bedrooms: 3

Bathrooms: 2 & 1 Half Bath

Minimum Stay: 3 nights

Peaceful retreat with breathtaking sunsets located on Tilghman Island. Kayaking, sailing, fishing, are all with in 100 feet of this beautiful home. Take a walk or a Bike ride to explore this unique island community. Visit Phillips Wharf Environmental Center and the Watermen’s Museum to learn all about life on the Chesapeake Bay. Enjoy dining in one of the islands many restaurants, rent a jet ski or paddle board at the marina. But then again, you may want to just sit on the water’s edge and enjoy the tranquility of this unique property.

Endless Sunset, Claiborne MD

Sleeps: 4

Bedrooms: 2

Bathrooms: 3 & 1 Half Bath

Minimum Stay: 3 nights

Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Eastern Shore of MD. Slow your pace and enjoy a leisurely bike ride into town or stroll the public beach for sea glass, unusual shells or driftwood. Lounge poolside with a good book or enjoy the ever-present cool breezes from the porches. Or, just do nothing at all…. You won’t believe the views from the double-decker waterside porches of this lovely 3 BR/3.5 BA home. Claiborne boasts some of the most beautiful sunsets you’ve ever seen over Eastern Bay! If you’re looking for a quaint get-away spot with plenty to do — or not!! — Endless Sunsets is the place to spend your vacation days. We’d be honored to have you and you’ll be glad you decided to visit. We hope you have a pleasant stay and welcome you to return again with friends and family.

The Cove, Sherwood MD

Sleeps: 10

Bedrooms: 5

Bathrooms: 4 & 3 Half Baths

Minimum Stay: 3 nights

The Cove At St. Michaels is a magnificent professionally decorated 15.5 acre estate property, just a 15 minute drive to the center of the Town of St. Michaels, and is the perfect location for a vacation with family and friends. With its 5 bedrooms (with hypo-allergenic encasement covers on all mattresses, pillows and box springs), 7 bathrooms, 2 full kitchens, 2 living rooms, and 2 dining rooms, our home sleeps 10+ and offers enough space for our guests to all be together – or for some guests to have their alone time and separate space.. Our home is child-friendly with its basketball hoop, play area and Wii XBOX 360 consoles. The 4 DirecTV-connected TVs (including 65′, 42” and 32” HD TVs all with DVD players) provide separate entertainment opportunities for children and adults alike. Located on the water, with 230 feet of shoreline, our home’s wrap-around screened-in porch and second open-air porch afford the opportunity to enjoy spectacular views of the peaceful Cove and its various wildlife (swans, ducks, geese, heron, to name a few). Or enjoy similar views from the private fenced-in pool and spa area. Our 150+’ dock and its 20’ by 10’ deck provide the opportunity to enjoy the water “up close and personal,” just sitting back and relaxing, fishing or crabbing. The dock’s 4’ MLW depth should allow you toh ujlhjl;jlv,; milk,oor your boat with little concern for the tides and our location make both the Choptank River and the Chesapeake Bay easily accessible.

Tilghman Time, Tilghman, MD

Sleeps: 8

Bedrooms: 4

Bathrooms: 2 & 1 Half Baths

Minimum Stay: 3 nights

Within minutes of historic St Michaels this 4 BEDROOM waterfront home is located on Tilghman Island. A watermen’s community offering everything you need to relax and enjoy a REAL Eastern Shore vacation. A private dock on the Knapps Narrows is just the spot to launch your kayak or dock your boat. The kids will love fishing and crabbing right on the waters edge. When inside this tastefully decorated coastal property you will feel right at home. The first floor with wide open floor plan, well appointed kitchen and large island is perfect for gathering with family and friends. The first floor master en-suite with water view will be the room everyone fights over!. On the second floor there is 3 additional bedrooms, full bath and a cozy loft to sneak away to. Walking distance of marinas and restaurants this waterfront home is the perfect place to put your feet up and watch the boats cruising the Knapps Narrows. We call this home “Tilghman Time” because when your on Tilghman one does not pay attention to time. Your having so much fun and relaxing that time sort of stands still.

Gracenote, Bozman, MD

Sleeps: 8

Bedrooms: 4

Bathrooms: 3

Minimum Stay: 3 nights

Just minutes from St Michaels this contemporary home is the perfect waterfront retreat. Offered for the first time this home gives its guest the peacefulness of tall pines lining a waters edge. Kayak, crab off the dock, take a dip in the pool or watch your family and friends as you sit with a book on the properties screened in porch. The kitchen is open to a spacious dining area and family room with panoramic views of the water. Step down into the living room with a fireplace furnished in a Scandinavian contemporary flair. Rounding out the first floor is a bedroom and full bath. The second floor has 2 additional bedrooms and a full bath and a master with private balcony overlooking the pool and water. At night enjoy gathering around the fire pit or taking a short drive into St Michaels to enjoy a fabulous meal at one of the many restaurants we have to offer. Grace Note allows its guest to get lost in its private peaceful setting or they may choose to go into town to shop, visit galleries or museums. Whichever you choose you wont be disappointed.

More Rentals Coming Soon!

Over 37 Years Of Dedicated Real Estate Experience

It’s our intention to provide the very best real estate services for our clients, regardless of whether they want to buy or sell a house, or lease property as a vacation rental. Please review our contact information to discover more.

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