Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND | House in Sherwood

10.0 (36 Reviews) |   8 Bedrooms  9 Bathrooms  12 Guests
Sherwood House | Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

8 Bedroom House in Sherwood

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

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND is located in Sherwood. Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND provides accommodation, featuring Air Conditioner, Accessibility, Sports/Activities, among other amenities. This House features Air Conditioner, Accessibility, Sports/Activities, to make your stay a comfortable one.

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND has 8 Bedrooms , 9 Bathrooms, and max occupancy of 12 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Sherwood has interesting places to visit. If you want to learn more about the House in Sherwood, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pool
TV
View
Wheelchair Accessible
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Accessibility
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Bathtub or shower
  • Shampoo
  • Toilet paper
  • 9 bathrooms
  • Hair dryer
  • Soap
  • Towels provided
Bedroom
  • Bed sheets provided
  • 8 bedrooms
  • Dining table
  • Living room
  • Fireplace
  • Dining room
Kitchen
  • Paper towels
  • Refrigerator
  • Toaster
  • Lobster/crab pot
  • Dishwasher
  • Oven
  • Microwave
  • Stovetop
  • Electric kettle
Laundry
  • Laundry facilities
  • Washing machine and dryer
  • Near laundromat
Ocean view
  • Beach sun loungers
  • Beach towels
Parking
  • Onsite parking
  • Onsite parking options include a garage
Pet Friendly
  • No pets allowed
Accessibility
  • Wheelchair accessible
  • Smoke-free property
  • Elevator
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Activities
  • Wildlife and game walks nearby
  • Marina nearby
  • Hunting nearby
  • Kayaking nearby
  • Golfing on site
  • Birdwatching nearby
  • Kayak on site
  • Golf privileges
  • Water tubing nearby
  • Rafting nearby
  • Bicycle on site
  • Horse riding nearby
  • Fitness center
  • Ecotours nearby
  • Fitness facilities nearby
Entertainment
  • Arcade/game room
  • Books
  • DVD player
  • Smart TV with cable/satellite service
  • Table tennis
  • Foosball table
  • Pool or billiards table
  • Games
General
  • Unit size: 12000 sq ft (1115 sq m)
  • Locally-owned & organized tours & activities
  • Local artist showcase
  • At least 80% lighting from LEDs
  • English
  • Near the bay
  • In a rural location
  • On the waterfront
  • Near a hospital
  • Near outlet shopping
  • On the river
  • Near the sea
  • Near a health or beauty spa
  • Desk
  • Office
  • Desk chair
Guest Services
  • Playground
  • Stair gate
  • Children's dinnerware
  • Children's books
  • Children's toys
  • Children's games
  • Highchair
  • Housekeeping (on request)
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Firepit
  • Barbecue grill
  • Outdoor furniture
  • Patio
  • Garden
Security/Safety
  • Fire extinguisher
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • First aid kit
Spa
  • Private pool
  • Heated pool
  • Outdoor pool
  • Fence around the pool

Policies

Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property long-term renters welcome onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

helen w.
Jul 9, 2025 09:26:02 PM
Review Score:   10
Summary: This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely adorable town to visit or have dinner in. Highly recommend.
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