House in Maryland
10 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Talbot County MD Short Term Rental License #STRN-23-12
Arrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5-bdr, 3.5-bth retreat with its own private pier near the historic and charming town of St. Michaels. Enjoy breathtaking waterfront views from the expansive decks, complete with a gourmet grill for al fresco dining and a cozy backyard fire pit perfect for relaxing with a cold brew or glass of your favorite wine. Your private pier awaits you for fishing, crabbing, kayaking and paddle board (all provided)
There are multiple cozy entertainment spaces for your enjoyment. Relax and unwind in the large living room, featuring a large screen TV with high-speed WiFi and 180-degree water views. Enjoy the natural light and serene ambiance of the sunroom, overlooking Oak Creek. Take in the stunning water views from the comfort of the 2nd floor ensuite bedroom and gathering area with a panoramic view of Oak Creek also with a wide screen TV. Retreat to the front reading room of the house for a quiet moment, conversation or to read a book and look out over the serene landscape.
Please be aware that the swing adorning our tree at the front of the house is for decorative purposes only and is not to be used as such.
You will be in the most convenient of locations. Just a 2 minute walk to the Oaks Resort with dining and jazz several times a week. Historic St. Michaels is a 5 minute drive with its charming stores, multiple dining venues and the Chesapeake Bay Maritime Museum. Explore the beauty of Oxford and the many activities, unique shops, and restaurants in Easton.
Our Talbot County License #STRN--23-12 permits 10 GUESTS in our house and property at any given time. Please note that our Talbot County Short Term Rental license requires a three night minimum and does not allow any events to be held on the property. We are located in a serene, residential community in Royal Oak and Talbot County has a noise ordinance - no noise after 10 PM No pets permitted.
Highlights
o 5 min drive to historic St. Michaels
o 2 min walk to the Oaks Resort
o beautiful water views
o large deck areas
o private pier for fishing, crabbing & kayaking/boating
o custom coffee & tea bar; complimentary whole bean coffee, grinder, coffee selection
o fully equipped kitchen
o gas fireplace
o outdoor fire pit
o outdoor gourmet(new Weber Genisus) barbecue
o 2 large screen TV, Cable & Disney Channel for the kids
o high speed internet
o game collection box and kids room with DVD's and player
o horseshoes, cornhole, badminton and other games
o fishing rods and tackle box
o TESLA charging port
o 240 v, NEMA EV charging port
o Two main bedrooms - one on first floor and one on second floor with three additional bedrooms and large sitting room with window wall overlooking the water.
o Spaces for gathering and spaces for quiet reflections and/or me time.
Arrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5-bdr, 3.5-bth retreat with its own private pier near the historic and charming town of St. Michaels. Enjoy breathtaking waterfront views from the expansive decks, complete with a gourmet grill for al fresco dining and a cozy backyard fire pit perfect for relaxing with a cold brew or glass of your favorite wine. Your private pier awaits you for fishing, crabbing, kayaking and paddle board (all provided)
There are multiple cozy entertainment spaces for your enjoyment. Relax and unwind in the large living room, featuring a large screen TV with high-speed WiFi and 180-degree water views. Enjoy the natural light and serene ambiance of the sunroom, overlooking Oak Creek. Take in the stunning water views from the comfort of the 2nd floor ensuite bedroom and gathering area with a panoramic view of Oak Creek also with a wide screen TV. Retreat to the front reading room of the house for a quiet moment, conversation or to read a book and look out over the serene landscape.
Please be aware that the swing adorning our tree at the front of the house is for decorative purposes only and is not to be used as such.
You will be in the most convenient of locations. Just a 2 minute walk to the Oaks Resort with dining and jazz several times a week. Historic St. Michaels is a 5 minute drive with its charming stores, multiple dining venues and the Chesapeake Bay Maritime Museum. Explore the beauty of Oxford and the many activities, unique shops, and restaurants in Easton.
Our Talbot County License #STRN--23-12 permits 10 GUESTS in our house and property at any given time. Please note that our Talbot County Short Term Rental license requires a three night minimum and does not allow any events to be held on the property. We are located in a serene, residential community in Royal Oak and Talbot County has a noise ordinance - no noise after 10 PM No pets permitted.
Highlights
o 5 min drive to historic St. Michaels
o 2 min walk to the Oaks Resort
o beautiful water views
o large deck areas
o private pier for fishing, crabbing & kayaking/boating
o custom coffee & tea bar; complimentary whole bean coffee, grinder, coffee selection
o fully equipped kitchen
o gas fireplace
o outdoor fire pit
o outdoor gourmet(new Weber Genisus) barbecue
o 2 large screen TV, Cable & Disney Channel for the kids
o high speed internet
o game collection box and kids room with DVD's and player
o horseshoes, cornhole, badminton and other games
o fishing rods and tackle box
o TESLA charging port
o 240 v, NEMA EV charging port
o Two main bedrooms - one on first floor and one on second floor with three additional bedrooms and large sitting room with window wall overlooking the water.
o Spaces for gathering and spaces for quiet reflections and/or me time.
Amenities at Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Non-smoking
No pets allowed
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Sep 2025
Lovely property on the Chesapeake Bay. Quiet community-easy drive to St.Michaels. House fully equipped with everything you could want! Good biking area. Highly recommend!!
10 / 10Outstanding·Sep 2025
Beautiful home and property. Most well equipped kitchen I have seen in a rental home. Excellent location, with only a 5 minute drive to downtown St. Michael's. Stayed at the home for a girls' weekend and several of my friends want to return to the house with their families!
10 / 10Outstanding·Aug 2025
Exactly as described except for one bedroom’s layout. Fully stocked kitchen, beautiful view, lots of gathering spaces, glorious weather. Boat slip allowed us to bring our own. Wonderful family retreat.
10 / 10Outstanding·Aug 2025
Amazing location, gorgeous house, and great communications from our host. We can't say enough wonderful things about the stay at Chesapeake Landing. The house is as advertised and looks just like the pictures. We had two families of 4 staying there and hosted a celebratory birthday dinner for my mother in law's 75th. The kitchen is soooo well equipped and has anything and everything you could possibly need to cook some amazing meals. The house is set up really nicely for hosting multiple families and my daughters and niece really enjoyed the kids bedroom that has 3 single beds. All of the bedding and furniture are comfortable and well appointed. We used the badminton net, both kayaks, and the standup paddleboard. All of us spent time fishing and crabbing and we even managed to catch 5 fairly large blue crabs and a few decent size fish. We will definitely plan to return. My wife even discussed the idea of trying to buy the place. Thanks for an amazing stay!
$$$$
Top rated by guests
10Outstanding
(53 Ratings)
"Lovely property on the Chesapeake Bay. Quiet community-easy drive to St.Michaels. House fully equipped with everything you could want! Good biking area. Highly recommend!!"
Katherine H.Don't miss out! Price and availability may change
