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.

Dunmoyle
STN-23-12

Sleeps: 8

Bedrooms: 4

Bathrooms: 3

Minimum Stay: 3 nights

This charming 16+ acre waterfront farmhouse circa 1769 just underwent a massive renovation and interior redesign for a beautiful Eastern Shore get-a-way. The house is situated adjacent to the water on a circular drive at the end of a quarter mile driveway through the forest, and past a 200 year old red barn, fields and fruit trees. The home has beautiful and private park-like grounds with a large, newly resurfaced in-ground pool, and water access from approximately 750 feet of water frontage on Grace Creek and a substantial dock which has 5’ MLW depth and which provides excellent opportunities for crabbing and fishing. The house offers breathtaking sunsets over Grace Creek from almost every room. It has 4 bedrooms, a den with a spectacular view of the water, 3 full baths, 2 living rooms, a dining room and 3 porches (front porch, screened in back porch and porch on second floor of the back of the house) all of which offer extraordinary views of the water only 15 feet away. Needless to say there is ample space for your groups' relaxation & comfort together. The property comes with bikes and canoes for your enjoyment, as well as hammocks, a fire pit and outdoor furniture. Visitors also enjoy hiking through the beautiful forests on the grounds. Conveniently located in Bozman, only a 10 minute drive to the lovely town of St. Michaels which features excellent restaurants and shopping. The house is fully wired for high speed internet and tv is available via Hulu. You will no doubt have a fantastic time.

Sunset Cottage, Tilghman Island MD
STRN-23-37

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.

Simplicity Cottage
STRN-23-58

Simplicity Cottage is a beautiful 2 bed with 1.5 bath waterfront home that offers peace and relaxation. The home sits comfortably on 0.35 acres and has a substantial dock around the back for your use. This home is located on Tilghman Island where you can rent kayaks, Canoes, and bikes. You may also do fishing trips with the multiple charters the Island has to offer. Surrounded by the beautiful Chesapeake Bay your options are endless.

Sleeps: 4

Bedrooms: 2

Bathrooms: 1 & 1/2 Baths

Minimum Stay: 3 nights

Happy Place,Tilghman Island MD
STN-22-40

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
STRN-23-22

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
STRN-23-16

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

Gracenote, Bozman, MD
STN-23-30

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.

Chesapeake Landing, MD
STRN-23-12

Bedrooms: 5

Bathrooms: 4

You will arrive at your destination to find a beautiful 4000+sq. ft., 2 story waterfront home with its own pier nestled just 5 minutes from historic St. Michaels and near Oxford & Tilghman Island.

Newly furnished and spattered w/vintage pieces, your 5 bedroom, 4 bathroom vacation stay boasts expansive water views from the living room, dining room, sunroom and upstairs sitting room. Wake up in your large master bedroom with a direct water view to the sun rising. Enjoy the evening activity sitting out on the large fully furnished deck looking out to the water. Perfect for relaxing with a cold brew or glass of your favorite wine and fully equipped for outdoor grilling. Step into the backyard and enjoy the private pier where you can fish, crab, and kayak. Everything you need is here and ready for you to enjoy your stay.

Perry Point, MD
STRN-22-40

Sleeps: 6

Bedrooms: 3

Bathrooms: 4

Minimum Stay: 3 nights

Come slip away for a while and Imagine staying in this private 2-acre fresh new totally customized farmhouse with 150+-year-old random width oak floors, a true chef's kitchen, fireplace, oversized screen porch, outdoor pizza oven, and also a heated pool. second-floor observation deck, and a game room with shuffleboard. Carefully selected furniture and linens and Gorgeous views from every direction of this home. Less than 2 miles from downtown Saint Michaels. Easy boat ride to Saint Michael's harbor from our pier. Elevated and professionally landscaped lot. Overlooks Porter Creek, and the Miles River. Enjoy our resident eagles and ospreys. Catch crabs from the pier or simply lay in the hammock and enjoy the day. Come see for yourself you will not be disappointed. BOOK PERRY POINT TODAY.

Eventide
ST-217-FLU

Sleeps: 8

Bedrooms: 4

Bathrooms: 3

Minimum Stay: 3 nights

Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This meticulously designed vacation home is tailored for the ultimate relaxation and adventure, offering a seamless blend of comfort, luxury, and outdoor excitement.

Picture yourself returning from an exhilarating day on the Bay, gently mooring your boat to the private dock before plunging into the refreshing pool. In the morning, experience the thrill of crabbing right off the dock, hoping for a fresh catch that could turn into a delightful feast. Explore the serene island surroundings on a bike or kayak, immersing yourself in nature's beauty.

Rain or shine, the deck and the inviting 3-season room await, where you can sizzle up a storm on the BBQ and enjoy your culinary creations. Engage in friendly competitions with a game of horseshoes or simply unwind in the comfortable ambiance of your vacation haven.

Inside, an airy and spacious open floor plan welcomes you, seamlessly connecting the well-stocked kitchen, living, and dining areas. Whether you prefer an intimate dinner or a lively family gathering, the two dining spaces cater to your every need. For the younger ones, there's a designated bean bag room filled with games and puzzles, ensuring endless entertainment.

Retreat to one of the four cozy guest rooms, each providing private, immaculate, and soothing accommodations. Families will appreciate the convenience of the family-style suite, making travel with little ones effortless. The three full bathrooms, including one conveniently located near the pool area, boast modern amenities, adding a touch of luxury to your stay. Your ideal waterfront retreat awaits where unforgettable moments and cherished memories are just a booking away.

More Rentals Coming Soon!

Over 39 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.

Name(Required)