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RANCH AT ROYAL OAK- Exclusive waterfront pool pier

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Dining
Golf
Interior
Interior
Interior

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms6 bathroomsSleeps 12427 sq m

Popular amenities

  • Barbecue grill
  • Washer
  • Pool
  • Dryer
  • Kitchen
  • Outdoor space

Explore the area

View map
Royal Oak, MD
  • St. Michaels Winery
    ‪21 min drive‬
  • St. Michaels Marina
    ‪22 min drive‬
  • Chesapeake Bay Maritime Museum
    ‪23 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪32 min drive‬

Room options

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  • Pool
  • Kitchen
  • Washer
  • Dryer
5.0 out of 5, Exceptional, 35 reviews
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About the area

Royal Oak

With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 7.8 mi (12.6 km) from Saint Michaels Village and 8.3 mi (13.3 km) from St. Michaels Winery. .This family-friendly vacation home is 8.4 mi (13.6 km) from St. Michaels Museum and 8.5 mi (13.7 km) from Windon Distilling.
View more Holiday homes in Royal OakOpens in a new window

What's nearby

  • Saint Michaels Village - 19 min drive - 14.4 km
  • St. Michaels Winery - 21 min drive - 15.8 km
  • St. Michaels Marina - 22 min drive - 16.5 km
  • Chesapeake Bay Maritime Museum - 23 min drive - 17.2 km
  • Oxford Museum - 25 min drive - 6.5 km

Getting around

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

Restaurants

  • ‪Carpenter Street Saloon - ‬20 min drive
  • ‪Foxy's Harbor Grille - ‬20 min drive
  • ‪Rise Up Coffee - ‬17 min drive
  • ‪Rusticana (St. Michael's) - ‬18 min drive
  • ‪The Blue Crab - ‬20 min drive

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

Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment.
Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. This vacation home also features an arcade/game room and barbecue grills.
Guests will find features like internet access and onsite parking.

Property amenities

Pool/Spa

  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • 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.
  • In-room accessibility
  • Smoke-free property

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 centre
  • 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)

General

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

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

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
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

RANCH AT ROYAL OAK- Exclusive waterfront pool pier Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 25 out of 26 reviews
Rating 8 - Good. 1 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Janette O.

Liked: Cleanliness
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

10/10 Excellent

Kate F.

Liked: Cleanliness

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

10/10 Excellent

Nicole N.

Liked: Cleanliness

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

10/10 Excellent

Ned I.

Liked: Cleanliness

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

10/10 Excellent

Tim D.

Liked: Cleanliness

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

10/10 Excellent

Erik S.

Liked: Cleanliness

Great place

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

10/10 Excellent

Karen S., Somers Point , New Jersey

Liked: Cleanliness

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

10/10 Excellent

Cheryl D.

Liked: Cleanliness

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

10/10 Excellent

Tina N.

Liked: Cleanliness

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

10/10 Excellent

Kellie M.

Liked: Cleanliness

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

10/10 Excellent

Matt Z.

Liked: Cleanliness

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

8/10 Good

William M.

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

10/10 Excellent

joe n.

Liked: Cleanliness

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

10/10 Excellent

susan f.

Liked: Cleanliness

Family celebration

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

10/10 Excellent

Fred V.

Liked: Cleanliness

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

10/10 Excellent

Matthew W.

Liked: Cleanliness

Great views and privacy

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

10/10 Excellent

Cory B.

Liked: Cleanliness

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

10/10 Excellent

julia e.

Liked: Cleanliness

Great property

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

10/10 Excellent

Jeff P.

Liked: Cleanliness

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

10/10 Excellent

Shelley S., Catonsville, MD

Liked: Cleanliness

Amazing

Everything about the place was spectacular. Our family spent 3 nights in this beautiful home and we were all very impressed. Everything about it was perfect! I would definitely recommend staying here.
Stayed 3 nights in Oct 2022

10/10 Excellent

Kathy M.

Liked: Cleanliness

It was perfect! The house was beautiful and clean. The weather was perfect. Owners were awesome!

This was a wonderful get away place for my friends and I. The house had everything we needed and we relaxed and enjoyed our time away. Now we all want a shuffleboard at our houses! It was perfect!😊
Stayed 3 nights in Oct 2022

10/10 Excellent

Mindy H.

Liked: Cleanliness

WONDERFUL!

Lovely location & property; the sunsets at the back of the house were the icing on the cake of this clean & beautifully appointed home. Wonderful for the group of 10 that we had in terms of bedroom size, bathrooms, and places to gather. Would highly recommend this property.
Stayed 4 nights in Oct 2022

10/10 Excellent

Kelly S.

Liked: Cleanliness

Excellent Property

Our family (6 adults, 6 young children) had an excellent stay at this property that is exactly as advertised. It has been recently updated, is well maintained, and comfortably appointed. We especially appreciated the cleanliness, owner responsiveness, property location and amenities available to guests. It is a beautiful retreat and we definitely recommend it!
Stayed 5 nights in Sep 2022

10/10 Excellent

Abbey W.

Liked: Cleanliness

Amazing Chesapeake Retreat

We spent a wonderful week at the Ranch with a group of friends that have been vacationing in the area for over five years. The house is beautiful, spacious, and incredibly well-stocked with everything we needed for a week of relaxation. No design detail was overlooked- truly like living in a magazine spread. The combination and layout of bedrooms made everyone feel comfortable - no one was stuck in a random basement bunk room like is so often the case in larger vacation homes. Ryan and Marissa were gracious hosts and we are so grateful to have experienced this slice of Chesapeake a la Austin in our own backyard.
Stayed 7 nights in Jul 2022

10/10 Excellent

Lisa M.

Liked: Cleanliness

Wedding Week

Royal Oak was a beautiful property to host our family leading up to our daughter and son-in-laws wedding at Chesapeake Bay Maritime Museum! The house is spacious to accommodate large families while providing cozy areas to have everyone gather in the dining areas and game rooms! We loved the pool and kayaking on the bay! Marissa was easy to communicate with and she answered our requests/questions right away. It was a dream vacation & wedding week! Thank you for having us at your lovely home!
Stayed 5 nights in Jul 2022