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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Photo gallery for Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

A golf course with multiple water hazards and a large pond.
A large, multi-story brick building with a symmetrical facade, a central entrance with columns, and a flagpole with an American flag.
A room with a round table and four wicker chairs, large windows with a view of a grassy field and the ocean, and a white wall.
A two-story house with a swimming pool, surrounded by a white fence and lush greenery.
A modern kitchen with a central island, white cabinetry, and green chairs.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • On-site fitness center
    A rare find - enjoy convenient access to fitness facilities during your stay.
  • Unmatched views, unforgettable moments
    Guests like the location for the scenic views.
8 bedrooms8+ bathroomsSleeps 12

Popular amenities

  • Private pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Sherwood, MD
  • Place, Knapp's Narrows Marina & Inn
    ‪6 min drive‬
  • Place, Back Creek Community Park
    ‪6 min drive‬
  • Place, Tilghman Island Marina
    ‪7 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪44 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

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 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 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

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Elevator must be requested in advance. Specify on lease. Proof of identification required Lease returned within 48 hours.

Important information

You need to know

Property # 2207416vb
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and hiking/biking trails nearby.
View more Holiday homes in SherwoodOpens in a new window
Map
Sherwood, MD

What's nearby

  • Knapp's Narrows Marina & Inn - 6 min drive - 4.5 km
  • Back Creek Community Park - 6 min drive - 4.5 km
  • Tilghman Island Marina - 7 min drive - 5.8 km
  • Tilghman Watermen’s Museum - 7 min drive - 6.5 km
  • Phillips Wharf Environmental Center - 7 min drive - 6.2 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 39 min drive

Restaurants

  • ‪Gina’s @ The Bridge - ‬6 min drive
  • ‪Big Mack's Kitchen & Dock Bar - ‬6 min drive
  • ‪Two if by Sea - ‬7 min drive

Frequently asked questions

Does Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

As of 26 Aug, 2026, prices found for a 1-night stay for 2 adults at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND on 29 Nov, 2026 start from S$7,958, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND pet-friendly?

No, pets are not allowed at this property.

How much is parking at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

On-site parking is available at the property.

What time is check-in at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

Check-in begins at 4:00 PM.

What time is check-out at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

Checkout is at 10:00 AM.

Where is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND located?

This family-friendly Sherwood holiday home is located on the waterfront, within 3 mi (5 km) of Knapp's Narrows Marina & Inn, Phillips Wharf Environmental Center and Back Creek Community Park. Goat Island and Kronsberg Park are also within 3 miles (5 km).

About the host

Hosted by Marissa

Host profile image
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.

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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