Entire home
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





Reviews
1010 out of 10
Exceptional
Entire home
8 bedrooms9 bathroomsSleeps 121115 sq m
Popular amenities
- Fireplace
- Dryer
- Washer
Explore the area

Sherwood, MD
- Tilghman Watermen’s MuseumPlace, Tilghman Watermen’s Museum8 min drive
- Chesapeake Bay Maritime MuseumPlace, Chesapeake Bay Maritime Museum28 min drive
- St. Michaels WineryPlace, St. Michaels Winery29 min drive
- Easton, MD (ESN-Easton - Newnam)Airport, Easton, MD (ESN-Easton - Newnam)52 min drive
Room options
Similar properties

RANCH AT ROYAL OAK- Exclusive waterfront pool pier
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Royal Oak
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 26 reviews
5
Exceptional
26 reviews

Breathtaking Waterfront Estate
Breathtaking Waterfront Estate
Neavitt
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 71 reviews
5
Exceptional
71 reviews

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Sherwood
- Pool
- Hot tub
- Kitchen
- Washer
5.0 out of 5, Exceptional, 16 reviews
5
Exceptional
16 reviews

Heated pool, sandy beach, pier, and playground set punch point apart!
Heated pool, sandy beach, pier, and playground set punch point apart!
Sherwood
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 10 reviews
5
Exceptional
10 reviews

Thorneton Point Estate
Thorneton Point Estate
Easton
- Pool
- Hot tub
- Kitchen
- Washer
4.8 out of 5, Exceptional, 20 reviews
4.8
Exceptional
20 reviews

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Royal Oak
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 90 reviews
5
Exceptional
90 reviews

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
St. Michaels
- Pool
- Hot tub
- Kitchen
- Washer
4.3 out of 5, Excellent, 4 reviews
4.3
Excellent
4 reviews

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Tilghman
- Pool
- Kitchen
- Washer
- Dryer
4.8 out of 5, Exceptional, 7 reviews
4.8
Exceptional
7 reviews

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
Easton
- Pool
- Kitchen
- Washer
- Dryer
5.0 out of 5, Exceptional, 2 reviews
5
Exceptional
2 reviews

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Stevensville
- Kitchen
- Washer
- Dryer
- Free WiFi
5.0 out of 5, Exceptional, 41 reviews
5
Exceptional
41 reviews
About the area
Sherwood
Located in Sherwood, this vacation home is by the sea, within a 10-minute drive of Back Creek Community Park and Knapp's Narrows Marina & Inn. .This family-friendly vacation home is 2.7 mi (4.4 km) from Goat Island and 2.8 mi (4.5 km) from Phillips Wharf Environmental Center.
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
- Easton, MD (ESN-Easton - Newnam) - 39 min drive
Restaurants
- Gina’s @ The Bridge - 6 min drive
- Two if by Sea - 7 min drive
- Tickler's Crab Shack and Restaurant - 7 min drive
- P T Hambleton Seafood - 25 min drive
- Bridge Restaurant - 6 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.
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
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a private pool. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. A Smart television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected.
Take advantage of recreation opportunities including an outdoor pool and a fitness center. This vacation home also features an arcade/game room and barbecue grills.
Featured amenities include laundry facilities and an elevator.
Property amenities
Beach
- Beach loungers
- Beach towels
Pool/Spa
- Heated pool
- Outdoor pool
- Private pool
Internet
- Available in the house: Free WiFi
Parking and transport
- Onsite parking options include a garage
Kitchen
- Blender
- Coffee grinder
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Electric kettle
- Hob
- Ice maker
- Kitchen island
- Lobster/crab pot
- Microwave
- Oven
- Paper towels
- Refrigerator
- Spices
- Toaster
Dining
- Dining table
Bedrooms
- 8 bedrooms
- Bedsheets provided
Bathroom
- 9 bathrooms
- Bathtub
- Bathtub or shower
- Hair dryer
- Shampoo
- Shower
- Soap
- Toilet paper
- Towels provided
Living spaces
- Dining table
- Fireplace
- Living room
- Separate dining area
Entertainment
- Books
- DVD player
- Games
- Smart TV with cable/satellite channels
Outdoor areas
- Barbecue grill
- Firepit
- Garden
- Outdoor furniture
- Patio
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Desk
- Desk chair
- Office
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
- Lift
- 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
- Near the sea
- On a river
- On the waterfront
Things to do
- Arcade/game room
- Bicycles
- Billiards/pool table
- Foosball table
- Golf
- Gym
- Heated pool
- Kayak
- Optional golf privileges
- Table tennis
- Birdwatching nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Hiking/biking trails nearby
- Horseback riding nearby
- Hunting nearby
- Jet skiing nearby
- Kayaking nearby
- Motor boating nearby
- Rafting nearby
- Sailing nearby
- Swimming nearby
- Water skiing nearby
- Water tubing nearby
- Wildlife walks 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)
- First aid kit
- Fire extinguisher
- Deadbolt lock
General
- At least 80% lighting from LEDs
- Bicycles
- Garden
- Housekeeping (on request)
- Local artist showcase
- Locally-owned and organised tours and activities
- Unit size: 12,000 square feet
Policies
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
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
Property is also known as
Chesapeake Mansion 12 000 Sqft/ 30 Acres
Chesapeake Mansion 12 000 Sqft/ 30 Acres/ Heated Pool
CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES Sherwood