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

10.0 (37 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, Pool, Wheelchair Accessible, among other amenities. This House features Air Conditioner, Pool, Wheelchair Accessible, 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
  • Towels provided
  • Bathtub or shower
  • Shampoo
  • Soap
  • 9 bathrooms
  • Toilet paper
  • Hair dryer
Bedroom
  • Bed sheets provided
  • 8 bedrooms
  • Dining table
  • Fireplace
  • Living room
  • Dining room
Kitchen
  • Oven
  • Lobster/crab pot
  • Microwave
  • Paper towels
  • Coffee/tea maker
  • Stovetop
  • Electric kettle
  • Dishwasher
  • Refrigerator
Laundry
  • Near laundromat
  • Washing machine and dryer
  • Laundry facilities
Ocean view
  • Beach sun loungers
  • Beach towels
Parking
  • Onsite parking
  • Onsite parking options include a garage
Pet Friendly
  • No pets allowed
Accessibility
  • Elevator
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Smoke-free property
  • Wheelchair accessible
Activities
  • Fitness facilities nearby
  • Golf nearby
  • Golfing on site
  • Sailing nearby
  • Bicycle on site
  • Fitness center
  • Water skiing nearby
  • Water tubing nearby
  • Marina nearby
  • Wildlife and game walks nearby
  • Swimming nearby
  • Birdwatching nearby
  • Fishing nearby
  • Kayak on site
  • Golf privileges
Entertainment
  • DVD player
  • Games
  • Pool or billiards table
  • Smart TV with cable/satellite service
  • Books
  • Arcade/game room
  • Table tennis
  • Foosball table
General
  • Local artist showcase
  • At least 80% lighting from LEDs
  • Locally-owned & organized tours & activities
  • Unit size: 12000 sq ft (1115 sq m)
  • English
  • Near a health or beauty spa
  • On the river
  • In a rural location
  • Near a hospital
  • On the waterfront
  • Near the sea
  • Near the bay
  • Near outlet shopping
  • Desk
  • Desk chair
  • Office
Guest Services
  • Children's dinnerware
  • Children's toys
  • Children's games
  • Playground
  • Stair gate
  • Children's books
  • Highchair
  • Housekeeping (on request)
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Patio
  • Barbecue grill
  • Outdoor furniture
  • Garden
  • Firepit
Security/Safety
  • First aid kit
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
Spa
  • Fence around the pool
  • Outdoor pool
  • Heated pool
  • Private 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

James S.
Aug 7, 2025 03:24:13 AM
Review Score:   10
Summary: We went to Sherwood to celebrate a family event. The house was perfect - lots of room for everyone. Check-in was simple, house was in excellent condition and the owners made every effort to accommodate our needs (some extra equipment for little kids). We enjoyed the pool and the beautiful setting. Great stay!
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