Entire home
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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Reviews
10 out of 10
Exceptional
8 bedrooms 8+ bathrooms Sleeps 12 1114.8 sq m
Popular amenities
Explore the area

Sherwood, MD
- Tilghman Watermen’s Museum8 min drive
- Chesapeake Bay Maritime Museum28 min drive
- St. Michaels Winery29 min drive
- Easton, MD (ESN-Easton - Newnam)52 min drive
Rooms & beds
8 bedrooms (sleeps 12)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
3 Double Beds
Bedroom 4
1 King Bed
Bedroom 5
1 King Bed
Bedroom 6
1 King Bed
Bedroom 7
2 Queen Beds and 1 Crib
Bedroom 8
1 King Bed
8 bathrooms, 2 half bathrooms
Bathroom 1
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 3
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Bathroom 4
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Bathroom 5
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Bathroom 6
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Bathroom 7
Soap · Towels provided · Toilet · Shower only · Shampoo
Bathroom 8
Soap · Towels provided · Toilet · Shower only · Shampoo
Bathroom 9
Soap · Toilet
Bathroom 10
Soap · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Office
Separate dining area
Outdoor play area
Garden
Dining area
About this property
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
TREMEZZO STAY - CHEASAPEAKE MANSION
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 or are looking for a more moderate price point please visit our other listings!
Ranch at Royal Oak:
https://www.vrbo.com/2697100?unitId=3267863
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Spencer Creek Cabin:
https://www.vrbo.com/1342430?unitId=1900766
Chesapeake Mansion is the premier Eastern Shore destination.
Voted #1 mansion rental in the state of Maryland by “Trips to Discover”!
Voted "Coolest ABNB in the state of Maryland" by Conde Nast Traveler (December 2021).
Also was host to the Bravo TV Network’s Real Housewives of Potomac.
The pool is open from mid-March to mid-October and to answer your question.. YES, it is heated :) This enormous 12,000 sqft. home sits on a private 30 acres just outside of St. Michaels. We spent 2 years updating this home with all of your rental needs in mind. This home sleeps the county maximum of 12 guests.
Please take a look at the virtual tour if you have a moment!
•August 2022- New playground surround installed
•October 2021- 160’ pier installed with 5’ MLW
•August 2021- New poly-wood mega playground installed
•March 2021- Atlantic Broadband has officially been added along with an EXTENSIVE MESH WiFi network!!!
Talbot County Rental License: ST-214-LYT
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 or are looking for a more moderate price point please visit our other listings!
Ranch at Royal Oak:
https://www.vrbo.com/2697100?unitId=3267863
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Spencer Creek Cabin:
https://www.vrbo.com/1342430?unitId=1900766
Chesapeake Mansion is the premier Eastern Shore destination.
Voted #1 mansion rental in the state of Maryland by “Trips to Discover”!
Voted "Coolest ABNB in the state of Maryland" by Conde Nast Traveler (December 2021).
Also was host to the Bravo TV Network’s Real Housewives of Potomac.
The pool is open from mid-March to mid-October and to answer your question.. YES, it is heated :) This enormous 12,000 sqft. home sits on a private 30 acres just outside of St. Michaels. We spent 2 years updating this home with all of your rental needs in mind. This home sleeps the county maximum of 12 guests.
Please take a look at the virtual tour if you have a moment!
•August 2022- New playground surround installed
•October 2021- 160’ pier installed with 5’ MLW
•August 2021- New poly-wood mega playground installed
•March 2021- Atlantic Broadband has officially been added along with an EXTENSIVE MESH WiFi network!!!
Talbot County Rental License: ST-214-LYT
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Sherwood
Located in Sherwood, this holiday home is in a rural area and on the waterfront. Knapp's Narrows Marina & Inn and Tilghman Island Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Back Creek Community Park and Goat Island. Travelling with kids? Consider Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Sherwood, MD
What's nearby
- Tilghman Island Marina - 8 min drive - 5.5 km
- Tilghman Watermen’s Museum - 8 min drive - 6.5 km
- St. Michaels Marina - 28 min drive - 25.3 km
- Chesapeake Bay Maritime Museum - 28 min drive - 25.3 km
- St. Michaels Winery - 29 min drive - 26.0 km
Getting around
Restaurants
- Gina’s @ The Bridge - 6 min drive
- Two if by Sea - 7 min drive
- Marker Five - 6 min drive
- Tickler's Crab Shack and Restaurant - 7 min drive
- Bridge Restaurant - 6 min drive
Frequently asked questions
About the host
Hosted by Marissa

We’ve always shared a passion for travel, home renovation, decor - and Italian food! So creating luxury experiences for others rooted in what we personally love just felt right.
And we hope you feel that love when you stay with us - each home has been handpicked and extensively outfitted with our guests’ comforts in mind. We personally manage each property so we consistently deliver the direct attentiveness you and your loved ones deserve throughout your entire experience.
We take pride in uniquely designing our homes based on what matters to you. We work hand-in-hand to give you more than just a space to land, but an unforgettable place to LIVE.
When we’re not curating luxury experiences for our guests, we’re spending time with our three young daughters in the St. Michaels area whenever humanly possible.
And we hope you feel that love when you stay with us - each home has been handpicked and extensively outfitted with our guests’ comforts in mind. We personally manage each property so we consistently deliver the direct attentiveness you and your loved ones deserve throughout your entire experience.
We take pride in uniquely designing our homes based on what matters to you. We work hand-in-hand to give you more than just a space to land, but an unforgettable place to LIVE.
When we’re not curating luxury experiences for our guests, we’re spending time with our three young daughters in the St. Michaels area whenever humanly possible.
Why they chose this property
Hi! We’re Brandon and Marissa. We’ve lived in Maryland for over 15 years, but it wasn’t until we discovered the Eastern Shore that we fully committed to calling Maryland home. When we visited St Michaels and the surrounding area for the first time…well, it was love at first visit!
What makes this property unique
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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