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

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Welcome to TREMEZZO STAY - CHEASAPEAKE MANSION, the premier Eastern Shore destination in St. Michaels, MD. This luxurious 12,000 sqft home offers a heated pool from mid-March to mid-October and sits on 30 private acres with plenty of space for relaxation and play.

Reviews

10 out of 10
Exceptional

Entire home

8 bedrooms9 bathroomsSleeps 121115 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning

Add dates for prices

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 amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Wheelchair-accessible parking available
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 8 bedrooms
  • Bedsheets provided

Bathroom

  • 9 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Accessible parking space
  • In-room accessibility
  • Lift
  • Wheelchair-accessible parking
  • Smoke-free property

Services and conveniences

  • Housekeeping on request
  • Iron/ironing board

Location highlights

  • In a rural location
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the sea
  • On a river
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Foosball table
  • Golf
  • Gym
  • Heated pool
  • Kayak
  • Optional golf privileges
  • Table tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Rafting nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • Bicycles
  • Garden
  • Housekeeping (on request)
  • Local artist showcase
  • Locally-owned and organised tours and activities
  • Unit size: 12,000 square feet

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  • Pool
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9.6 out of 10, Exceptional, 390 reviews
The price is NZ$1,261
includes taxes & fees
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Policies

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Elevator must be requested in advance. Specify on lease. Proof of identification required Lease returned within 48 hours.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
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

About the area

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 ecotours nearby. Visit our Sherwood travel guide
View more Holiday homes in Sherwood
Map
Sherwood, MD

What's nearby

  • Back Creek Community Park
    6 min drive - 4.5 km
  • Knapp's Narrows Marina & Inn
    6 min drive - 4.5 km
  • Tilghman Island Marina
    7 min drive - 5.8 km
  • Talbot County Library Tilghman Branch
    7 min drive - 6.2 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
  • Big Mack's Kitchen & Dock Bar
    6 min drive
  • Marker Five Waterfront Dining
    6 min drive
  • Gina’s @ The Bridge
    6 min drive
  • Tickler's Crab Shack and Restaurant
    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.

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).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 37 out of 38 reviews
Rating 8 - Good. 1 out of 38 reviews
Rating 6 - Okay. 0 out of 38 reviews
Rating 4 - Poor. 0 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 reviews

10

Cleanliness

9.8

Location

Reviews

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

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

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

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

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

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

Sandra L.

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
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

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

Adam H.

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

Reunion

Great stay
Stayed 4 nights in Jul 2024
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

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

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

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

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

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