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

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Entire home

August 2022 - New playground area complete!

Links at Perry Cabin- please inquire with us directly if interested in play

Overview
Amenities
Policies
Location
Host

Exceptional

8 bedrooms8+ bathroomsSleeps 1212000 sq ft

Popular amenities

Fireplace
Dryer
Barbecue grill
Washer
Kitchen

Explore the area

Sherwood, MD

Tilghman Watermen’s Museum
‪7 min drive‬
Chesapeake Bay Maritime Museum
‪21 min drive‬
St. Michaels Winery
‪21 min drive‬
Easton, MD (ESN-Easton - Newnam)
‪39 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

Languages

English

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Pool
Kitchen
Washer
Dryer

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 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

Onsite parties or group events are strictly prohibited

Long-term renters welcome

Host has indicated there is a carbon monoxide detector on the property

Host has indicated there is a smoke detector on the property

Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Sherwood

Located in Sherwood, this vacation 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. Traveling with kids? Consider Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum. Be sure to check out the area's animals with activities such as game walks and birdwatching.

Sherwood, MD

What's nearby

Tilghman Watermen’s Museum - 7 min drive - 5.2 km
St. Michaels Marina - 20 min drive - 18.6 km
Chesapeake Bay Maritime Museum - 21 min drive - 18.7 km
St. Michaels Winery - 21 min drive - 18.9 km
U.S. Naval Academy - 92 min drive - 103.0 km

Getting around

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

Restaurants

‪Two If By Sea - ‬7 min drive
‪Marker Five - ‬6 min drive
‪Tickler's Crab Shack and Restaurant - ‬7 min drive
‪Bay Hundred Restaurant - ‬6 min drive
‪Characters Bridge 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.

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 vacation 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 mi (5 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Matt K.

Mar 30, 2025

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

10/10 Excellent

robert r.

Nov 14, 2024

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

10/10 Excellent

Adam H.

Aug 4, 2024

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

Reunion

Great stay

Stayed 4 nights in Jul 2024

10/10 Excellent

Richard S.

Apr 27, 2024

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

Matt H.

Aug 17, 2024

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

10/10 Excellent

Kevin R.

Sep 10, 2023

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

10/10 Excellent

Daniel S.

Jul 11, 2023

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

10/10 Excellent

Robin T.

Aug 27, 2022

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

10/10 Excellent

Liz W.

Aug 1, 2023

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

10/10 Excellent

Jen D.

Jan 8, 2024

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

10/10 Excellent

Deanna R.

Apr 1, 2024

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

8/10 Good

Joanne Y.

Jun 16, 2024

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

10/10 Excellent

Hillery Y., Bowie, Maryland

Jan 28, 2024

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

Margery L.

Sep 11, 2021

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

10/10 Excellent

kim d.

Feb 22, 2023

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

10/10 Excellent

Anne J.

May 2, 2023

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

Dee Dee

Jul 29, 2023

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

10/10 Excellent

Brian H.

Apr 18, 2023

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

10/10 Excellent

Rachel B.

Aug 23, 2023

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

10/10 Excellent

Robert G.

Apr 9, 2023

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

10/10 Excellent

Sandi C., Washington, DC

Jul 12, 2022

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

10/10 Excellent

Sarah C.

Apr 25, 2023

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

Incredible!

We were a party of 8 old girlfriends who have gotten pickier and pickier with age for our annual get together. The house, location and Marissa were all incredible. Beautifully appointed, kitchen well stocked with everything including consumables and so much space both inside and out. Comfort, quiet and privacy. So many bathrooms! Yeah! While likely designed for families (fantastic playground, pool, huge yard and lots of fun activities inside and out) it works well for all kinds of groups. Excellent prompt communication. The sunsets and the grand white oak as we winded down the day. A flock of turkeys, bald eagle, great blue herons, Bluebirds etc and the power of a thunderstorm one evening allowed lots of connection between friends and nature. Incredible.

Stayed 4 nights in Apr 2023

10/10 Excellent

Sandra L.

Oct 17, 2023

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

Girls Trip then Family

For my 50th and 60th birthday, I celebrated with 10 dear girlfriends in Bethany and then Annapolis. Now it was my 70th and I wanted something extra special with plenty of room and comfortable sleeping arrangements. Wow, I definitely found it at the Chesapeake Mansion! We spent 5 days doing yoga in the early morning while watching the eagles and osprey overhead. We cooked fabulous meals in the beautiful, fully equipped kitchen. We sang karaoke in the fabulous bar as we had cocktails and then watched the sun go down around a bonfire eating s’mores. It was sooooo perfect and Marissa was just amazing. Everyone wants to return, although we will definitely not wait 10 years!!! Next, my family arrived for another 5 days. It was totally different but also just PERFECT! My grandchildren swam everyday in the heated pool and played on the perfect playground. When we had a rainy day, the large playroom stocked with toys and a great play kitchen kept everyone happy. When the kids went down, the adults had plenty of space to have drinks, play pool, ping pong and some more karaoke! We also caught some crabs off the pier…..my grandchildren had a ball and can’t wait for my next birthday LOL!!! What a fantastic experience!

Stayed 10 nights in Oct 2023

10/10 Excellent

Cheryl T.

Oct 21, 2022

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

Awesome Home

You can't want for more from the multitude of king BRs with ensuite baths to a milk froth machine for your morning cup of joe. The kitchen was extremely well equipped. Our group consisted of 5 couples that met in college 40+ years ago. We've somewhat scattered to other states and have never gotten together more than one evening at a wedding for many years. Besides the pool and ping pong table and a foos ball table, they had a karaoke machine which while using created many memories that'll last a lifetime. Our only issue was the weather! We were there during the last dregs of Hurricane Ian but thankfully this property provided lots of entertainment options. We had no issues with the house other than not being able to find the firewood for the outdoor fire pit. A quick text that was responded to immediately sent us on our way. Can't say enough good things about this property. We didn't have any children with us but it is extremely well equipped to handle a gaggle of kids.

Stayed 5 nights in Oct 2022

10/10 Excellent

Lynn B.

Sep 19, 2022

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

Beautiful!!!

The property is beautiful; the views beautiful! Marissa was very responsive to any questions or requests. The pool and property are great. The house is stocked with basically anything you need - from pool towels, games, toys, and then the view!!

Stayed 4 nights in Sep 2022

About the host

Hosted by Marissa

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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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

Reviews

Popular amenities

Explore the area

Rooms & beds

8 bedrooms (sleeps 12)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

Bedroom 5

Bedroom 6

Bedroom 7

Bedroom 8

8 bathrooms, 2 half bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

Bathroom 8

Bathroom 9

Bathroom 10

Spaces

About this property

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

Property manager

Languages

Add dates for prices

Amenities

Have a question?

Similar properties

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RANCH AT ROYAL OAK- Exclusive waterfront pool pier

House Rules

Children

Events

Pets

Smoking

Important information

You need to know

About the neighborhood

Sherwood

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

10/10

10/10

10/10

10/10

10/10

Reviews

10/10 Excellent

Matt K.

Relaxing waterfront family reunion

Matt K.

10/10 Excellent

robert r.

Friends weekend

robert r.

10/10 Excellent

Adam H.

Reunion

Adam H.

10/10 Excellent

Richard S.

Great long weekend

Richard S.

10/10 Excellent

Matt H.

Great Experience

Matt H.

10/10 Excellent

Kevin R.