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

Property grounds
Pool
August 2022 - New playground area complete!
Links at Perry Cabin- please inquire with us directly if interested in play
Property grounds
Reviews
10 out of 10 Exceptional
8 bedrooms8+ bathroomsSleeps 121114.8 sq m

Popular amenities

  • PoolPoolPool
  • FireplaceFireplaceFireplace
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer
  • Air conditioningAir conditioningAir conditioning

Enjoy the area

Map
Sherwood, MD
  • Popular LocationTilghman Watermen’s Museum7 min drive
  • Popular LocationChesapeake Bay Maritime Museum21 min drive
  • Popular LocationSt. Michaels Winery21 min drive
  • AirportSalisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)93 min drive

Rooms & beds

8 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

3 Double Beds

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 King Bed

Bedroom 7

2 Queen Beds and 1 Crib

Bedroom 8

1 King Bed

8 bathrooms, 2 half bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 4

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 5

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 6

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 7

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 8

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 9

Soap · Toilet

Bathroom 10

Soap · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Separate dining area
Outdoor play area
Garden
Dining Area

About this property

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

Property manager

Marissa
Premier Host
Premier Host

Languages

English

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

House Rules

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted
Elevator must be requested in advance. Specify (add request)on last page of the lease.

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Sherwood

Located in Sherwood, this holiday home is in a rural area and on the waterfront. St. Michaels Winery and Rod n Reel Charter Fishing are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sandy Point State Park and Matapeake State Park. Travelling with kids? Consider Chesapeake Bay Maritime Museum, or check out an event or a game at Navy-Marine Corps Memorial Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Sherwood, MD

What's nearby

  • Phillips Wharf Environmental Center - 6 min drive
  • Tilghman Watermen’s Museum - 7 min drive
  • Chesapeake Bay Maritime Museum - 21 min drive
  • St. Michaels Winery - 21 min drive
  • U.S. Naval Academy - 92 min drive

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 39 min drive

Restaurants

  • Marker Five - 6 min drive
  • Two If By Sea - 7 min drive
  • Tickler's Crab Shack - 7 min drive
  • Harrison's Chesapeake House - 7 min drive
  • Island Cafe - 7 min drive

Frequently asked questions

Does Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND pet-friendly?

No, pets are not allowed at this property.

Where is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND located?

This family-friendly Sherwood holiday home is located on the waterfront, 3.2 mi (5.2 km) from Tilghman Watermen’s Museum, and within 12 mi (20 km) of Chesapeake Bay Maritime Museum and St. Michaels Museum. St. Michaels Winery is 11.7 mi (18.9 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 28 out of 28 reviews" "
Rating 8 - Good. 0 out of 28 reviews" "
Rating 6 - Okay. 0 out of 28 reviews" "
Rating 4 - Poor. 0 out of 28 reviews" "
Rating 2 - Terrible. 0 out of 28 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Richard S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great long weekend
Host and property were great
Stayed 4 nights in Apr 2024

10/10 Excellent

Anne J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect home for a family get-together
The property and home are beautiful and so comfortable! Our family had a wonderful gathering. Marissa was very helpful and always available. Thank you!
Stayed 3 nights in Apr 2023

10/10 Excellent

Deanna R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful extended Easter weekend
This property is just gorgeous inside and out! We were rained in a few days and did not have any trouble finding our fun! Lots of indoor activities and beautiful views! The kitchen is a fun family friendly atmosphere where all can hang out. Amazing time with our family in the prestigious home!
Stayed 4 nights in Mar 2024

10/10 Excellent

Hillery Y., Bowie, Maryland

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Waterfront Retreat
My friends and I had a spectacular time at this truly amazing property. The house is gorgeous and has every amenity you could possibly dream of wanting. Everything was clean, comfortable and the views were incredible. The hosts were responsive and everything was in perfect working order. Thank you for letting us stay in such wonderful accommodations!
Stayed 3 nights in Jan 2024

10/10 Excellent

Jen D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Manson House
Amazing house in an amazing location with wonderful owners! Fun house for a weekend with friends. Highly recommend. Fully stocked kitchen and so many amenities.
Stayed 3 nights in Dec 2023

About the host

Hosted by Marissa

Host profile image
We’ve always shared a passion for travel, home renovation, decor - and Italian food! So creating luxury experiences for others rooted in what we personally love just felt right.
And we hope you feel that love when you stay with us - each home has been handpicked and extensively outfitted with our guests’ comforts in mind. We personally manage each property so we consistently deliver the direct attentiveness you and your loved ones deserve throughout your entire experience.
We take pride in uniquely designing our homes based on what matters to you. We work hand-in-hand to give you more than just a space to land, but an unforgettable place to LIVE.
When we’re not curating luxury experiences for our guests, we’re spending time with our three young daughters in the St. Michaels area whenever humanly possible.

Why they chose this property

Hi! We’re Brandon and Marissa. We’ve lived in Maryland for over 15 years, but it wasn’t until we discovered the Eastern Shore that we fully committed to calling Maryland home. When we visited St Michaels and the surrounding area for the first time…well, it was love at first visit!

What makes this property unique

Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.

Languages:

English

Premier Host

Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback

More Holiday Rentals ideas