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RANCH AT ROYAL OAK- Exclusive waterfront pool pier

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Exterior - RANCH AT ROYAL OAK- Exclusive waterfront pool pier (Royal Oak)
Outdoor pool - RANCH AT ROYAL OAK- Exclusive waterfront pool pier (Royal Oak)
Exterior - RANCH AT ROYAL OAK- Exclusive waterfront pool pier (Royal Oak)
6 bedrooms, desk, iron/ironing board, free WiFi - RANCH AT ROYAL OAK- Exclusive waterfront pool pier (Royal Oak)
Dining - RANCH AT ROYAL OAK- Exclusive waterfront pool pier (Royal Oak)
Nestled in the exclusive Royal Oak area of St. Michaels, MD, The Ranch at Royal Oak offers an idyllic retreat. With its private yet proximate location to Easton and St. Michaels, this majestic peninsula provides a unique blend of exclusivity and convenience.

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms6 bathroomsSleeps 124600 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

TREMEZZO STAY - RANCH AT ROYAL OAK
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.

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

Property amenities

Pool/Spa

  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 5.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 accessible parking space
  • No elevator (single-level property)
  • Wheelchair accessibility
  • Wheelchair-accessible parking
  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In a rural location
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Golf
  • Kayak
  • Optional golf privileges
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • At least 80% lighting from LEDs
  • Bicycles
  • Garden
  • Housekeeping (on request)
  • Local artist showcase
  • Locally-owned and organized tours and activities
  • Unit size: 4,600 square feet

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Kent Island Resort
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  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
9.2 out of 10, Wonderful, 137 reviews
The price is CA $245
CA $319 total
includes taxes & fees
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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age: 30

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Rules

Once confirmed you will be required to sign our rental agreement prior to occupying the property

A picture ID of the guest executing the property’s terms and conditions is required prior to check-in

NO EVENTS. 12 guest maximum at all times. There are no additional guests permitted. Please adhere to the posted occupancy of the property at all times

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Located in Royal Oak, this vacation home is in a rural area and on the waterfront. St. Michaels Museum and Classic Motor Museum are cultural highlights, and some of the area's landmarks include Avalon Theatre and Easton Rail Depot. Traveling with kids? Consider Chesapeake Bay Maritime Museum and Easton Cycle and Sport. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and ecotours nearby. Visit our Royal Oak travel guide
View more Vacation homes in Royal Oak
Map
Royal Oak, MD

What's nearby

  • st michaels village maryland old historical houses
    Saint Michaels Village
    16 min drive - 14.8 km
  • Boats docked in the harbor, in St. Michaels, Maryland.
    St. Michaels Marina
    18 min drive - 16.8 km
  • Chesapeake Bay Maritime Museum
    Chesapeake Bay Maritime Museum
    19 min drive - 17.5 km
  • St. Michaels Winery
    17 min drive - 16.1 km
  • St. Michaels Museum
    18 min drive - 16.5 km

Getting around

  • Cambridge Station
    49 min drive
  • Easton, MD (ESN-Easton - Newnam)
    28 min drive

Restaurants

  • Foxy's Harbor Grille
    20 min drive
  • The Crab Claw
    21 min drive
  • Ava's Pizzeria & Wine Bar - St Michaels
    19 min drive
  • Doc's Sunset Grille
    39 min drive
  • t at The General Store
    12 min drive

Frequently asked questions

Does RANCH AT ROYAL OAK- Exclusive waterfront pool pier have a pool?

Yes, this property has an outdoor pool.

Is RANCH AT ROYAL OAK- Exclusive waterfront pool pier pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at RANCH AT ROYAL OAK- Exclusive waterfront pool pier?

Check-in begins at 4:00 PM.

What time is check-out at RANCH AT ROYAL OAK- Exclusive waterfront pool pier?

Check-out is at 11:00 AM.

Where is RANCH AT ROYAL OAK- Exclusive waterfront pool pier located?

Located on the waterfront, this family-friendly vacation home is within 9 mi (15 km) of Saint Michaels Village, Chesapeake Bay Maritime Museum, and Saint Marys Square. Church Cove Park and Back Creek Park are also within 9 mi (15 km).

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RANCH AT ROYAL OAK- Exclusive waterfront pool pier Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 30 out of 31 reviews
Rating 8 - Good. 1 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

RoseMarie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the best time! The house was spotless, had everything we could possibly need, and was the ideal spot for our entire group. Plus, the location is gorgeous and a super fast trip into St. Michael's. We'd come back in a heartbeat!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

ned b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Erik S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Perfect for a group gathering! Incredible views.
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Ned I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved It

Great place for a family getaway, the rooms were great and so was the pool. The activities shed was clean and orderly and had everything you'd need.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Mary S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Kellie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house

We had a wonderful stay at this beautiful property. The house was well equipped and very clean. Host was very hospitable.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Matt Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

The house and property are beautiful! We had fantastic meals (and ice cream) in both St. Michaels and Easton which are a close/easy drive. The host is truly famtastic and extremely responsive!
Stayed 5 nights in Aug 2023
Verified

10/10 Excellent

Nicole N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic property

The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway.
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

Tim D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Vacation

Beautiful, well appointed home. The kitchen was well stocked with cookware, utensils, spices, soaps and other basics. The furniture and beds were very comfortable. There were lots of games, bikes and kayaks to keep the kids busy and active along with a nice size pool. The screened porch was a great spot for morning coffee and watching the crab boats go by, and an evening view of sunset over the water. The owner was very responsive to a couple of small issues we had during our stay.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Cheryl D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Customer Retreat for Hunting

Upon arrival the house was immaculately clean and very easy to access via keypad access code. We enjoyed watching AFC Football championship game on Sunday in the entertainment room. The bedrooms are all spacious and the beds were very comfortable. The kitchen/ dinning area was perfect for our crowd. The Pier offers spectacular views and enjoyed watching wildlife. We will definitely be back here soon and look forward to a summer time visit !!
Stayed 3 nights in Jan 2024
Verified

10/10 Excellent

Tina N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just Awesome

Is there anything these hosts didn’t think of? Linens, bath products, kitchen utensils…it truly felt like home away from home. House was spotless upon arrival and host was responsive within minutes of any questions. The setting is tranquil and the waterfront was so pretty. Kids had fun on playground and with basketball hoop. We are looking forward to visiting again.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Karen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family time at the Ranch

The Ranch was an awesome spot for our family vacation. We had a massive Easter Egg Hunt on the huge property. The kids actually played in the water on Easter Sunday! Spent time in Saint Michael’s, Easton and Oxford ( all within 25 minutes). The house had plenty of space for us to hang out. Loved the large dining table! Melissa was a great host and kept in touch with me throughout the week. The house had everything we needed. We really appreciated the quick delivery of a fire pit! Thanks again Melissa!
Stayed 7 nights in Mar 2024
Verified

8/10 Good

William M.

Liked: Check-in, communication, location, listing accuracy

Bugtussle

The property was well laid out. Location very private. A few negatives that are easy fixes. There are companies that can spry acres of area for mosquitoes, spiders etc, this Property is right on the water and it is understood that the area will have insects in the area, however the amount of mosquitoes, tics and flys and small biting insects can be managed and guaranteed to eliminate thes pests. The other improvement needed is the WIFI it is Horrible, it was almost impossible to connect, with computers and iPADs Mobile devices send emails, or connect to Netflix etc. Access to enter water off the dock was not an easy entry. Need a ladder or a set of steps from the shore. It might be some kind of local code not to alter the rock shoreline to prevent erosion but we tried to kayak and it was very difficult and dangerous walking on the wet and sea grass covered large boulders. These are suggestions for the owners to make a beautiful place to stay, better and more Guest friendly. Not complaining just offering suggestions to improve the property. Nice layout and a great house.
Stayed 6 nights in Jul 2023
Verified

10/10 Excellent

Stephen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Kate F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Such a wonderful spot!!

Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon.
Stayed 5 nights in May 2025
Verified

10/10 Excellent

susan f.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family celebration

Great time for young and old.
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Matthew W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great views and privacy

Great property and views and privacy. Perfect for some secluded alone time.
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Janette O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ranch at Royal Oak is a great house with a spectacular host. The communication was stellar. The house is in excellent condition with everything you need right at the house. The kitchen is fully stocked with high end towels, linens, utensils, glasses, knives, bowls, plates, etc. The kids and adults loved the pool and fishing on the dock. Access to St. Michael's is very easy. We will be back!
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Robert c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

joe n.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magnificent retreat!

Amazing house and property. This was our second stay and would love to return! It's difficult to want for anything here!
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

julia e.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property

Beautiful comfortable home with lovely views. Well equipped, we would return.
Stayed 3 nights in Jan 2023
Verified

10/10 Excellent

Cory B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay

What a view! The photos of the property do not lie! We stayed with family for the weekend and had a wonderful time, despite the rain. The gathering spaces in the home are all perfect for large groups and the host was gracious and helpful. An A+ rental!
Stayed 3 nights in Apr 2023
Verified

10/10 Excellent

Fred V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ranch at Royal Oak

Beautiful home. Well appointed - everything needed for the kitchen, bathrooms entertainment is included. The property is private and the area is quite peaceful. The playground was a big hit. We hope to return to the Ranch in the future.
Stayed 5 nights in Jun 2023
Verified

10/10 Excellent

matt f.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible Home and Host

We had a fabulous stay at the Ranch at Royal Oak!! This place was incredible and a fantastic getaway for our family and friends! The ranch was exceptional; clean, beautifully decorated, spacious rooms with breathtaking water views . We had high hopes when we read about this lovely home and everything exceeded our expectations. The house was full of amenities that kept both the kids and adults entertained our entire stay. Marissa was a great communicator and responded to any questions we had immediately. Highly recommend! We can't wait to go back this summer! 5 stars plus!
Stayed 3 nights in Apr 2022
Verified

10/10 Excellent

Jeff P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Outstanding

This was a very peaceful setting on the water with plenty of space & land for the kids to go play. Every box gets checked at this house! The house is very well done inside and out! Highly recommend it to anyone!
Stayed 3 nights in Nov 2022