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

A golf course with multiple water hazards and a large pond. - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)
A two-story house with a swimming pool, surrounded by a white fence and lush greenery. - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)
A room with a round table and four wicker chairs, large windows with a view of a grassy field and the ocean, and a white wall. - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)
A coastal view with a stone jetty, grassy area, and white lounge chairs. - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)
A large, multi-story brick building with a symmetrical facade, a central entrance with columns, and a flagpole with an American flag. - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)
Golfing on-site, a firepit and a garden are just a few of the amenities provided at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND. Free in-room WiFi is available to all guests, along with a playground and an arcade/games room.

Reviews

10 out of 10
Exceptional

Entire home

8 bedrooms9 bathroomsSleeps 121115 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • 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 rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events.

    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
  • 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

  • Bicycles
  • Garden
  • Housekeeping (on request)
  • Local artist showcase
  • Locally-owned and organised tours and activities
  • Some LED lighting used
  • Unit size: 12,000 square feet

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  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 30

Check-out

Check-out before 10:00 AM

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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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 hiking and horse riding nearby. Visit our Sherwood travel guide
View more Holiday homes in Sherwood
Map
Sherwood, MD

What's nearby

  • A large suspension bridge over a calm body of water with a sunset in the background.
    Northern Chesapeake Bay
    7 min drive - 5.9 km
  • Knapp's Narrows Marina & Inn
    6 min drive - 4.5 km
  • Tilghman Island Marina
    7 min drive - 5.8 km
  • Tilghman Watermen’s Museum
    7 min drive - 6.5 km
  • Phillips Wharf Environmental Center
    7 min drive - 6.2 km

Getting around

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

Restaurants

  • Big Mack's Kitchen & Dock Bar
    6 min drive
  • Gina’s @ The Bridge
    6 min drive
  • Tickler's Crab Shack and Restaurant
    7 min drive
  • Two if by Sea
    7 min drive
  • Marker Five Waterfront Dining
    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.

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.

What time is check-in at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

Check-in begins at 4:00 PM.

What time is check-out at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

Checkout is at 10:00 AM.

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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Reviews

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

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 41 out of 42 reviews
Rating 8 - Good. 1 out of 42 reviews
Rating 6 - Okay. 0 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 reviews

Reviews

Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolute Perfection! The Best VRBO We Have Ever Stayed At.Don’t hesitate—just book it! Our family vacation at the Sherwood Mansion absolutely exceeded our expectations in every single way.Here are just a few reasons why this property is a 10/10:Better Than the Pictures: We were blown away when we walked inside. The entire property is stunning, and the pictures online simply don't do it justice. The kitchen, in particular, is much larger and more spacious than it appears in the photos—perfect for cooking for a large group.Peaceful, Serene, & Private: If you are looking for a true escape, this is it. The property offered an incredible amount of privacy, allowing our family to completely relax and unwind in peace.Fun for All Ages: There was never a dull moment. The pool was a massive hit for everyone, and we loved fishing right off the private boat dock. The playground and the kids' room were also way better than expected and kept the little ones joyfully busy.Epic Adult Amenities: Inside, the bar and karaoke setup were a huge hit and made for unforgettable family nights.Impeccably Clean: The mansion was spotless from top to bottom, which immediately made us feel comfortable and at home.Outstanding Hospitality: We had a family member traveling with a broken foot, which could have been a major challenge. However, the host, Marissa, went above and beyond by making the elevator available. Her thoughtfulness made our stay incredibly smooth and stress-free.
Stayed 6 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The mansion is exactly as advertised - spacious, beautifully designed interior, very nicely appointed - and the overall property is stunning. The sunsets behind the island across the water from the house are gorgeous. And Marissa is great - she is kind and very responsive. 10/10 experience overall, highly recommend.
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

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

Great long weekend

Host and property were great
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

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

Reunion

Great stay
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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