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

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your current months are November, 2024 and December, 2024.
November 2024
December 2024

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

Sun loungers, beach towels
Interior
Golf
Exterior
Dining

Reviews

10 out of 10

Exceptional

Entire home

8 bedrooms9 bathroomsSleeps 121114.8 sq m

Popular amenities

  • Washer
    Washer
  • Pool
    Pool
  • Barbecue grill
    Barbecue grill
  • Outdoor space
    Outdoor space
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

Explore the area

Map
Sherwood, MD
  • Tilghman Watermen’s Museum
    7 min drive
  • Chesapeake Bay Maritime Museum
    21 min drive
  • St. Michaels Winery
    21 min drive
  • Camp Springs, MD (ADW-Andrews Air Force Base)
    120 min drive

Room options

About the area

Sherwood

Seaside stay .At this Sherwood vacation home, you'll be within 6 miles (10 km) of Tilghman Watermen’s Museum and 12 miles (20 km) of Chesapeake Bay Maritime Museum. St. Michaels Museum and St. Michaels Winery are within 12 miles (20 km).
View more Vacation homes in SherwoodOpens in a new window

What's nearby

  • Tilghman Watermen’s Museum - 7 min drive
  • St. Michaels Museum - 20 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

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Languages

English

Property amenities

Beach

  • Beach towels
  • Beach sun loungers

Pool/Spa

  • Private pool
  • Outdoor pool
  • Heated pool
  • Fence around the pool

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking options include a garage
  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Electric kettle
  • Lobster/crab pot
  • Paper towels
  • Toaster

Dining

  • Dining table

Bedrooms

  • 8 bedrooms
  • Bed sheets provided

Bathrooms

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

Living spaces

  • Fireplace
  • Living room
  • Dining room

Entertainment

  • Smart TV with cable/satellite service
  • Pool or billiards table
  • Foosball table
  • Table tennis
  • Arcade/game room
  • DVD player
  • Games
  • Books

Outdoor areas

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

Laundry

  • Washing machine and dryer
  • Near laundromat

Work spaces

  • Office
  • Desk
  • Desk chair

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.
  • Elevator
  • Wheelchair accessible
  • Smoke-free property

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • Near the sea
  • On the river
  • On the waterfront
  • In a rural location
  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping
  • Near the bay

Things to do

  • Fitness center
  • Golf privileges
  • Fitness facilities nearby
  • Golfing on site
  • Bicycle on site
  • Kayak on site
  • Marina nearby
  • Kayaking nearby
  • Rafting nearby
  • Wildlife and game walks nearby
  • Horse riding nearby
  • Ecotours nearby
  • Water tubing nearby
  • Hunting nearby
  • Birdwatching nearby

Safety features

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

General

  • At least 80% lighting from LEDs
  • Local artist showcase
  • Locally-owned & organized tours & activities
  • Unit size: 12000 sq ft (1114.8 sq m)

Policies

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

Chesapeake Mansion 12 000 Sqft/ 30 Acres
Chesapeake Mansion 12 000 Sqft/ 30 Acres/ Heated Pool
CHESAPEAKE MANSION - HEATED POOL/ 12,000 SQFT/ 30 ACRES Sherwood

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

Reviews

10

Exceptional

Rating 10 - Excellent. 31 out of 32 reviews" "
Rating 8 - Good. 1 out of 32 reviews" "
Rating 6 - Okay. 0 out of 32 reviews" "
Rating 4 - Poor. 0 out of 32 reviews" "
Rating 2 - Terrible. 0 out of 32 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

robert r.

Liked: Cleanliness
Friends weekend
Perfect large space on a quiet and pretty area. Really great space.
Stayed 4 nights in Nov 2024

10/10 Excellent

Matt H.

Liked: Cleanliness
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

Adam H.

Liked: Cleanliness
Reunion
Great stay
Stayed 4 nights in Jul 2024

8/10 Good

Joanne Y.

Liked: Cleanliness
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

Richard S.

Liked: Cleanliness
Great long weekend
Host and property were great
Stayed 4 nights in Apr 2024

10/10 Excellent

Deanna R.

Liked: Cleanliness
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
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
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

Sandra L.

Liked: Cleanliness
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

Kevin R.

Liked: Cleanliness
Family getaway
Perfect spot for families with little kids. Great host and beautiful home.
Stayed 3 nights in Aug 2023

10/10 Excellent

Rachel B.

Liked: Cleanliness
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

Liz W.

Liked: Cleanliness
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

Dee Dee

Liked: Cleanliness
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

Daniel S.

Liked: Cleanliness
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

Anne J.

Liked: Cleanliness
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

Sarah C.

Liked: Cleanliness
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

Brian H.

Liked: Cleanliness
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

Robert G.

Liked: Cleanliness
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

kim d.

Liked: Cleanliness
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

Cheryl T.

Liked: Cleanliness
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.

Liked: Cleanliness
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

10/10 Excellent

Robin T.

Liked: Cleanliness
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

John C.

Liked: Cleanliness
Beautiful house on the Chesapeake Bay
Well maintained and recently updated with lots of room for a big family group. The house has plenty of amenities to keep everyone occupied inside and out. Everything works and the owner is very responsive.
Stayed 14 nights in Jul 2022

10/10 Excellent

Sandi C., Washington, DC

Liked: Cleanliness
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

terese d.

Liked: Cleanliness
Beautiful Waterfront with Heated Pool and Family Fun Favorites
After four years our large family was under the same roof for the first time. This beautiful VRBO had enough bedrooms and bathrooms to provide the privacy and vacation feel for all. We used the billard room almost every evening and the home is large enough that the noise did not disturb sleeping children. We had a couple of folks who were working from home and they had private quiet space for virtual meetings. They experienced a brief wi-fi outage but after sending a text to the host it was fixed within minutes. Phew! The children had a stocked playroom, our nightly family cooking challenge competition was a lot of fun in the large open kitchen (Sushi night was the winner with fresh tuna sourced from the local Wittman seafood store that was only 5 minutes away). The heated pool was a big hit and right next to the large playground so it kept us all together. The host had a multitude of yard games and we used croquet, can jam, and cornhole. Our 50 ft boat charter with captain was able to pick us up from the dock- no worries with water depth. We tried our luck at fishing from the dock and crabbing- no luck. Haha. We ordered crabs from nearby Chesapeake Landing restaurant for our last night and the kitchen was stocked with everything we needed to host our own crabfeast at home. This property sits directly on the open bay so swimming and paddleboarding were not possible. Having the boat charter allowed us to find nearby swimming holes and explore the area. We enjoyed the firepit, smores, beautiful sunsets, and morning country side walks/runs. The VRBO hosts were very responsive and helpful. Don’t hesitate to book it. This property is worth it :)
Stayed 7 nights in Jun 2022