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 Wellness Facilities, Air Conditioner, Pool, among other amenities. This House features Wellness Facilities, Air Conditioner, Pool, 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
  • Heating
  • Air conditioning
Bathrooms
  • Towels provided
  • Hair dryer
  • Toilet paper
  • Bathtub or shower
  • Soap
  • Shampoo
  • 9 bathrooms
Bedroom
  • Bed sheets provided
  • 8 bedrooms
  • Dining table
  • Living room
  • Dining room
  • Fireplace
Kitchen
  • Stovetop
  • Dishwasher
  • Kitchen island
  • Refrigerator
  • Microwave
  • Oven
  • Toaster
  • Ice maker
  • Cookware/dishes/utensils
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
  • Smoke-free property
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Elevator
  • Wheelchair accessible
Activities
  • Kayak on site
  • Cycling nearby
  • Wildlife and game walks nearby
  • Bicycle on site
  • Fitness facilities nearby
  • Hiking nearby
  • Winery tours nearby
  • Fitness center
  • Hiking/biking trails nearby
  • Horse riding nearby
  • Fishing nearby
  • Marina nearby
  • Golfing on site
  • Jet skiing nearby
  • Golf privileges
Entertainment
  • Pool or billiards table
  • Books
  • Arcade/game room
  • DVD player
  • Foosball table
  • Games
  • Table tennis
  • Smart TV with cable/satellite service
General
  • Unit size: 12000 sq ft (1115 sq m)
  • Locally-owned & organized tours & activities
  • Local artist showcase
  • At least 80% lighting from LEDs
  • English
  • On the river
  • Near a hospital
  • Near outlet shopping
  • Near the sea
  • Near the bay
  • Near a health or beauty spa
  • In a rural location
  • On the waterfront
  • Desk
  • Desk chair
  • Office
Guest Services
  • Children's books
  • Children's dinnerware
  • Children's games
  • Children's toys
  • Stair gate
  • Highchair
  • Playground
  • Iron/ironing board
  • Housekeeping (on request)
Internet
  • Free WiFi
Outdoors
  • Patio
  • Outdoor furniture
  • Garden
  • Barbecue grill
  • Firepit
Security/Safety
  • Deadbolt lock
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • First aid kit
  • Fire extinguisher
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
Spa
  • Fence around the pool
  • Outdoor pool
  • Private pool
  • Heated 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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