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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 travel advisors 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.

Choosing to book your vacation with one of our travel advisors will give you an advantage. It will not only save you
hundreds of dollars in booking fees but you will receive personal service that should come with a five-star property.
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.

Vacation Rental Home Information:

1. Sunset Cottage, Tilghman Island MD

  • Please contact office for pricing
  • Sleeps: 6
  • Bedrooms: 3
  • Bathrooms: 3
  • Min stay: 3 nights
  • License #: St-605-JOH

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.

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2. Happy Place,Tilghman Island

  • Please contact office for pricing
  • Sleeps: 6
  • Bedrooms: 3
  • Bathrooms: 2
  • Half Baths: 1
  • Min stay: 3 nights
  • License #: Forthcoming

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.

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3. Endless Sunset, Claiborne

  • Please contact office for pricing
  • Sleeps: 4
  • Bedrooms: 2
  • Bathrooms: 3
  • Half baths: 1
  • Min stay: 3 nights
  • License #: ST-482-LED

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.

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4. The Cove, Sherwood MD

  • Please contact office for pricing
  • Sleeps: 10
  • Bedrooms: 5
  • Bathrooms: 4
  • Half baths: 3
  • Min stay: 3 nights
  • License #: ST-217-SCH

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 to moor your boat with
little concern for the tides and our location make both the Choptank River and the Chesapeake Bay easily accessible.

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5. Tilghman Time, Tilghman, MD

  • Please contact office for pricing
  • Sleeps: 8
  • Bedrooms: 4
  • Bathrooms: 2
  • Half Baths: 1
  • Min stay: 3-7 nights
  • License #: STR # ST-217-HARG

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.

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