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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

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Exterior
Pool
August 2022 - New playground area complete!
Links at Perry Cabin- please inquire with us directly if interested in play
Exterior

Reviews

10 out of 10
Exceptional
8 bedrooms8+ bathroomsSleeps 12

Popular amenities

  • Private pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Sherwood, MD
  • Place, Knapp's Narrows Marina & Inn
    ‪6 min drive‬
  • Place, Back Creek Community Park
    ‪6 min drive‬
  • Place, Tilghman Island Marina
    ‪7 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪44 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

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Elevator must be requested in advance. Specify on lease. Proof of identification required Lease returned within 48 hours.

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. Knapp's Narrows Marina & Inn and Tilghman Island Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Back Creek Community Park and Goat Island. Travelling with kids? Consider Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and hiking/biking trails nearby.
View more Holiday homes in SherwoodOpens in a new window
Map
Sherwood, MD

What's nearby

  • Knapp's Narrows Marina & Inn - 6 min drive - 4.5 km
  • Back Creek Community Park - 6 min drive - 4.5 km
  • Kronsberg Park - 7 min drive - 5.8 km
  • Tilghman Island Marina - 7 min drive - 5.8 km
  • Tilghman Watermen’s Museum - 7 min drive - 6.5 km

Getting around

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

Restaurants

  • ‪Two if by Sea - ‬7 min drive
  • ‪Gina’s @ The Bridge - ‬6 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬7 min drive
  • ‪Marker Five Waterfront Dining - ‬6 min drive
  • ‪Bay Hundred Restaurant - ‬6 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.

How much does it cost to stay at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

As of 6 May 2026, prices found for a 1-night stay for 2 adults at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND on 7 May 2026 start from NZ$3,051, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

No, pets are not allowed at this property.

How much is parking at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

On-site parking is available at the 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, within 3 mi (5 km) of Knapp's Narrows Marina & Inn, Phillips Wharf Environmental Center and Back Creek Community Park. Goat Island and Kronsberg Park are also within 3 miles (5 km).

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. 36 out of 37 reviews
Rating 8 - Good. 1 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Ramin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an incredible experience! The house, pool, yard, view, and overall setting are stunning. The hosts were fantastic. Strongly recommend and would go back in a heartbeat.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

James S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sherwood Mansion

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!
Stayed 9 nights in Jul 2025
Verified

10/10 Excellent

Susan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion to visit again soon. Marissa is a fabulous host! Thank you!
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Adam H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Reunion

Great stay
Stayed 4 nights in Jul 2024
Verified

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
Verified

10/10 Excellent

Kevin R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family getaway

Perfect spot for families with little kids. Great host and beautiful home.
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Daniel S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Family House

This is a wonderful property for bigger families. It has plenty to do for all ages.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

robert r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends weekend

Perfect large space on a quiet and pretty area. Really great space.
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Robin T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous and relaxing

This is a beautiful home with an amazing view that has everything you could want for a restful vacation.
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Matt H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Experience

House was spacious, clean, and exactly as described in the listings. We had a great time!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Liz W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

House is great, so is owner

House was great, as advertised. The owner was very responsive, which is a huge plus for a rental house.
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Margery L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family get together

We had a grand time using the pool, and our 3 year old love the play gym in the yard. The sunsets were great.
Stayed 5 nights in Sep 2021
Verified

10/10 Excellent

kim d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing home fore a family reunion

11 family members, age range 8 moths to 88 years stayed in this beautiful home. Wonderful facilities for both adults and little ones. Marissa is a superb host. Very highly recommended.
Stayed 5 nights in Feb 2023
Verified

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
Verified

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
Verified

10/10 Excellent

Hillery Y.

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
Verified

10/10 Excellent

helen w.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home and tons of space

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.
Stayed 7 nights in Jun 2025
Verified

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
Verified

10/10 Excellent

Dee Dee

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful family vacation

Great place for two generations of family to gather. House and grounds were beautiful. All rooms very comfortable. Plenty of dishware and cooking equipment. Day trips to the ocean, Washington DC and Baltimore. St. Michaels, Easton and Tilghman Island were wonderful nearby spots. Host was very communicative and everything went perfectly smoothly.
Stayed 7 nights in Jul 2023
Verified

8/10 Good

Joanne Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends Tribal Bay Getaway

The Property Owners were both responsive and accommodating. The home is a lovely property and the venue is very nice with sweeping views of the Bay. There was plenty of space for our group of 10 to relax and congregate. Nice recreational areas with billiards, lovely pool and a fire pit as well as good beds, linens, dishes and appliances. The library of books was quite impressive as well.
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Matt K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing waterfront family reunion

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.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Brian H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceeded Expectations!

This property is even nicer in person than the pictures show online. Every guest was simply impressed with the size, cleanliness, and interior design of the property. The house came with everything you need to have fun playing lawn games (e.g., cornhole and croquet) make world class dinners, and keep the children occupied with a fully stocked game room and playground in the backyard. We had a ton of questions for the host and Melissa was super quick to reply with all the information we needed. We utilize VRBO quite often, and this was, by far, the nicest property we've stayed at. Even at the price point offered, it exceeded our expectations. We look forward to booking again in the future.
Stayed 3 nights in Apr 2023
Verified

10/10 Excellent

Robert G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to reconnect with family!

I recently stayed at the Chesapeake Mansion with my extended family for a week-long reunion. The property was accurately represented in the listing and provided an amazing experience for everyone in our group. The house was well-maintained, spacious, and had plenty of amenities to keep everyone entertained. The location was beautiful, with stunning sunsets in the evenings. One of the best things about our stay was communication with the owners. They were very responsive to any questions we had and made sure our stay was enjoyable. We appreciated their prompt communication and willingness to accommodate our needs. Overall, the Chesapeake Mansion was an incredible place to reconnect with family and create lasting memories. I would highly recommend this property to anyone looking for a large house to spend quality time with their loved ones.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Rachel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Idyllic and serene getaway with amazing views

This is a beautiful and well-maintained house with an incredible view, amazing pool, and great amenities for kids including one of the best private playgrounds I've ever seen and a lovely playroom stocked with toys. Our group had 5 kids ranging from 6 months to 5 years old, and we were very comfortable. Marisa was extremely communicative and helpful. It's a 15 min drive to St. Michael's but the property is extremely private and secluded so it's a great getaway from the city. The only thing that would have made our stay better is improved water pressure (it's fine if one person is using the shower at a time, but otherwise it gets quite low) -- but this wasn't a huge deal. Highly recommend.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Sandi C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful week. Great host!

This was a family vacation of 10 (6 adulats and 4 kids 6-9) celebrating our 50th anniversary. The house had so much room that everyone could spread out and do their own thing. The pool was incredible, sunset views, wildlife (on one tree alone, I took pictures of a bald eagle, 2 osprey and a great blue heron). The recreational amenities were super: playroom, games, billiards, foosball, karyoke, wifi speakers for music, cable tv with all the premium networks, a gym, etc. We all said we would stay for a week more if we could. Marissa and Brandon were amazing hosts. Very accommodating and responsive. Our only regret was that we really couldn't go into the bay with paddleboards or swim but the hosts made alternative arrangements for us to do that.
Stayed 7 nights in Jul 2022

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

They consistently provide great experiences for their guests
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