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

10.0 (35 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 Fireplace/Heating, Internet, Kitchen, among other amenities. This House features Fireplace/Heating, Internet, Kitchen, 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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Sherwood, 21665, USA

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
  • 9 bathrooms
  • Soap
  • Bathtub or shower
  • Shampoo
  • Toilet paper
  • Towels provided
  • Hair dryer
Bedroom
  • 8 bedrooms
  • Bed sheets provided
  • Dining table
  • Living room
  • Dining room
  • Fireplace
Kitchen
  • Coffee grinder
  • Stovetop
  • Refrigerator
  • Paper towels
  • Microwave
  • Lobster/crab pot
  • Cookware/dishes/utensils
  • Oven
  • Dishwasher
Laundry
  • Laundry facilities
  • Washing machine and dryer
  • Near laundromat
Ocean view
  • Beach sun loungers
  • Beach towels
Parking
  • Onsite parking options include a garage
  • Onsite parking
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
  • Golf privileges
  • Jet skiing nearby
  • Kayak on site
  • Water skiing nearby
  • Fitness center
  • Bicycle on site
  • Winery tours nearby
  • Hunting nearby
  • Fitness facilities nearby
  • Golfing on site
  • Horse riding nearby
  • Power boating nearby
  • Water tubing nearby
  • Ecotours nearby
  • Sailing nearby
Entertainment
  • Table tennis
  • Foosball table
  • Arcade/game room
  • Games
  • Books
  • Pool or billiards table
  • Smart TV with cable/satellite service
  • DVD player
General
  • At least 80% lighting from LEDs
  • Local artist showcase
  • Unit size: 12000 sq ft (1115 sq m)
  • Locally-owned & organized tours & activities
  • English
  • Near the bay
  • In a rural location
  • Near a health or beauty spa
  • Near the sea
  • Near a hospital
  • On the river
  • Near outlet shopping
  • On the waterfront
  • Office
  • Desk
  • Desk chair
Guest Services
  • Stair gate
  • Children's dinnerware
  • Children's toys
  • Highchair
  • Children's books
  • Playground
  • Children's games
  • Iron/ironing board
  • Housekeeping (on request)
Internet
  • Free WiFi
Outdoors
  • Barbecue grill
  • Garden
  • Firepit
  • Outdoor furniture
  • Patio
Security/Safety
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock
  • 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)
Spa
  • Private pool
  • Heated pool
  • Fence around the pool
  • Outdoor 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

Matt K.
Mar 31, 2025 01:57:39 AM
Review Score:   10
Summary: The Chesapeake Mansion was even better than it looks on the VRBO listing. Huge house but still managed to feel warm and inviting, never cold or stand-offish. We cooked big dinners for our group of 12 and the kitchen was perfect for that. Billiards room was fun, amazing bar room, also an exercise room. Walking out on the dock was always a treat. With 12 people, folks could always find a place to chill out when they wanted, but we also had big rooms where we could all get together for chatting and games.Would definitely come back here again! Also, the owner was very prompt at always getting back in touch when we had a couple questions.
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FAQ's

Is this Sherwood house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Sherwood house have a swimming pool?

Yes, this Sherwood house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Sherwood house?

Best-rates for the Sherwood house starts from $1,503 per night with includes Balcony/Terrace, Oceanfront, Parking, View, Accessibility, Wellness Facilities, Guest Services, Entertainment, Barbecue/Outdoor Cooking, Child Friendly, Security/Safety, Laundry, Air Conditioner, TV, Fireplace/Heating, Internet, Kitchen, Sports/Activities, Bedding/Linens, Pool, Wheelchair Accessible, Private Pool, Ocean View with all other facilities. BedroomVillas.ca matches every traveler with their perfect villa, resort, or rental and whether you are traveling with a group, friends, family, or pets.

Is Sherwood house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Sherwood house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Sherwood house is wheelchair accessible. Likewise, there is an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Sherwood house?

Based on the information reported by the owner or manager, the Sherwood house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Sherwood house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Sherwood house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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