House in Maryland
12 guests · 6 bedrooms · 5 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
TREMEZZO STAY - RANCH AT ROYAL OAK
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events.
If you do not see availability for your dates please visit our other exclusive listings!
Chesapeake Mansion:
https://www.vrbo.com/2207416?unitId=2771970
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Spencer Creek Cabin:
https://www.vrbo.com/1342430?unitId=1900766
Over the years we have had so many guests inquire about the Royal Oak area. Our response, of course, was to investigate what was generating of of the buzz. The results are in- exclusivity! This majestic peninsula is private yet so proximate to St. Michaels and Easton. After spending time at The Ranch at Royal Oak, believe me, you will understand. We're excited to offer this one-of-a-kind property to our guests!
Talbot County rental license ST-644-LYT
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events.
If you do not see availability for your dates please visit our other exclusive listings!
Chesapeake Mansion:
https://www.vrbo.com/2207416?unitId=2771970
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Spencer Creek Cabin:
https://www.vrbo.com/1342430?unitId=1900766
Over the years we have had so many guests inquire about the Royal Oak area. Our response, of course, was to investigate what was generating of of the buzz. The results are in- exclusivity! This majestic peninsula is private yet so proximate to St. Michaels and Easton. After spending time at The Ranch at Royal Oak, believe me, you will understand. We're excited to offer this one-of-a-kind property to our guests!
Talbot County rental license ST-644-LYT
Amenities at RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Non-smoking
No pets allowed
Family friendly
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Dec 2025
We had a wonderful week at the Ranch. 8 adults and four little ones. There was plenty of room both inside and out. The view of the water was spectacular! The outdoor swing/slide play area was used frequently. It was a little chilly for the fire pit (with complimentary s’mores fixin’s - so thoughtful!). The location was excellent - no nearby neighbors. But not far from St. Michaels and Easton. The kitchen was very well equipped and spacious - extra nice since we cooked nearly all of our meals there! We had a few issues while there and our host was very prompt in addressing them. All in all a wonderful week!
10 / 10Outstanding·Nov 2025
Great communication from owner. Well decorated. Very comfortable. Kids had ample space to play. Appreciated the separate kids play space with swingset. Would rent again!
10 / 10Outstanding·Oct 2025
My wife and I have stayed in some very nice locations, from a Grand suite on a cruise to a penthouse on the beach. We also own 2 time shares meaning we can go just about anywhere we want to go, however, The Ranch at Royal Oak topped them all. We were blown away by all the amenities and comforts available to us, if you are a time share owner you know you must think of everything (aluminum foil, spices, toiletries, firewood, etc.). But here all you need is a desire to do whatever you want to do; Relax, check, have fun til you drop, check, see one of the best sunsets on the planet, check. My advice, rent this home, you will not be sorry.
10 / 10Outstanding·Oct 2025
Each bedroom had en-suite bath or dedicated bath since first floor had a half bath which made it very nice for the 5 couples that stayed here. Also, was referred to personal chef and catering which made the birthday celebration very special.
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Top rated by guests
10Outstanding
(33 Ratings)
"We had a wonderful week at the Ranch. 8 adults and four little ones. There was plenty of room both inside and out. The view of the water was spectacular! The outdoor swing/slide play area was used fr..."
Mary S.Don't miss out! Price and availability may change
