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

Riverfront vacation home with a fitness center and an outdoor pool

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

Golf
Dining
Exterior
Sun loungers, beach towels
Exterior

Reviews

10 out of 10
Exceptional

Entire home

8 bedrooms9 bathroomsSleeps 1212000 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a 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)
    ‪43 min drive‬

Room options

About the neighborhood

Sherwood

This vacation home places you within a few miles (5 km) of Knapp's Narrows Marina & Inn and Back Creek Community Park. The vacation home includes a private pool, a kitchen, and a fireplace.
View more Vacation Homes in SherwoodOpens in a new window

What's nearby

  • Knapp's Narrows Marina & Inn - 6 min drive - 2.8 miles
  • Back Creek Community Park - 6 min drive - 2.8 miles
  • Tilghman Island Marina - 7 min drive - 3.4 miles
  • Phillips Wharf Environmental Center - 7 min drive - 3.4 miles
  • Tilghman Watermen’s Museum - 7 min drive - 4.1 miles

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

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
The vacation home is air-conditioned and features a kitchen, 9 bathrooms, and a patio. There's space to spread out with 8 bedrooms and a dining area. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a private pool, a washing machine, and a fireplace. Housekeeping is available on request.

Similar properties

Exterior
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
10.0 out of 10, Exceptional, 5 reviews
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • 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.
  • Elevator
  • Wheelchair accessibility
  • Smoking not allowed

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 mall
  • 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 organized tours and activities
  • Unit size: 12,000 square feet

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
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

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • Long-term renters welcome.

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

Frequently asked questions

What's there to do close to this vacation home?

This vacation home is located in Sherwood, close to Knapp's Narrows Marina & Inn, Tilghman Island Marina, and Tilghman Watermen’s Museum. You'll also find Back Creek Community Park and Goat Island within a short drive.

Is parking available on site at this vacation home?

Yes, there is a garage.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is an outdoor pool.

What do couples enjoy most about Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

At this historic vacation home, couples will welcome the many amenities including a private pool and a fireplace along with an outdoor pool.

Does Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND have a hot tub?

No, but this vacation home does have a heated pool.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, there aren't connecting rooms at this vacation home.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Easton, MD (ESN-Easton - Newnam), which is 24 mi away (39 minutes by car).

Are there rooms with balconies that I can book at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?

Yes, every accommodation at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND comes with a deck with some featuring water views.

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

Reviews

10

Exceptional

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

Reviews

10/10 Excellent

Susan P.

Liked: Cleanliness
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

10/10 Excellent

Ramin M.

Liked: Cleanliness
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

10/10 Excellent

James S.

Liked: Cleanliness

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

10/10 Excellent

helen w.

Liked: Cleanliness

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

10/10 Excellent

Matt K., San Francisco, CA

Liked: Cleanliness

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.

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