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!!!
dit vakantiehuis ligt in een landelijke omgeving en aan het water in Sherwood. Bezoek Knapp's Narrows Marina & Inn en Tilghman Island Marina als je graag iets actiefs wilt doen. Als je graag de natuur intrekt, verken dan Back Creek Community Park en Goat Island. Reis je met kinderen? Overweeg dan Phillips Wharf Environmental Center en Chesapeake Bay Maritime Museum. Kies voor waterpret zoals jetskiën of kajakken of beleef avonturen zoals wandelen en paardrijden. Bekijk onze reisgids voor Sherwood
Easton, Maryland (ESN-Easton - Newnam) - 39 min. rijden
Restaurants
Big Mack's Kitchen & Dock Bar
6 min. rijden
Gina’s @ The Bridge
6 min. rijden
Tickler's Crab Shack and Restaurant
7 min. rijden
Two if by Sea
7 min. rijden
Marker Five Waterfront Dining
6 min. rijden
Veelgestelde vragen
Beschikt Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND over een zwembad?
Ja, deze accommodatie heeft een buitenzwembad. Deze accommodatie beschikt onder meer over een verwarmd zwembad.
Zijn huisdieren welkom bij Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?
Nee, assistentiedieren zijn niet welkom bij deze accommodatie.
Hoeveel kost het om hier te parkeren?
Er zijn parkeerplaatsen beschikbaar bij de accommodatie.
Hoe laat kan ik bij Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND inchecken?
Inchecken is mogelijk vanaf 16.00 uur.
Tot hoe laat kan ik bij Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND uitchecken?
Je dient om uiterlijk 10.00 uur uit te checken.
Waar staat Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND?
Dit vakantiehuis gezinsvriendelijke dit vakantiehuis in Sherwood ligt aan het water, op 5 km afstand van Knapp's Narrows Marina & Inn, Phillips Wharf Environmental Center en Back Creek Community Park. Ook Goat Island en Kronsberg Park liggen op 5 km afstand.
Alle weergegeven beoordelingen zijn gebaseerd op echte gastenervaringen. Alleen reizigers die een verblijf bij ons hebben geboekt, kunnen een beoordeling indienen. We verifiëren beoordelingen op basis van onze richtlijnen en plaatsen alle beoordelingen, of ze nu positief of negatief zijn.Meer informatieOpent in een nieuw venster
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Beoordelingen
Geverifieerde beoordeling
10/10 – Voortreffelijk
Adam H.
4 aug 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Reunion
Great stay
4 nachten verbleven in juli 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
Christopher W.
23 mei 2026
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
5 nachten verbleven in mei 2026
Geverifieerde beoordeling
10/10 – Voortreffelijk
Kevin R.
10 sep 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Family getaway
Perfect spot for families with little kids. Great host and beautiful home.
3 nachten verbleven in augustus 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
robert r.
14 nov 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Friends weekend
Perfect large space on a quiet and pretty area. Really great space.
4 nachten verbleven in november 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
Richard S.
27 apr 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Great long weekend
Host and property were great
4 nachten verbleven in april 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
Ramin M.
22 sep 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
3 nachten verbleven in september 2025
Geverifieerde beoordeling
10/10 – Voortreffelijk
Daniel S.
11 jul 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Wonderful Family House
This is a wonderful property for bigger families. It has plenty to do for all ages.
7 nachten verbleven in juni 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
James S.
6 aug 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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!
9 nachten verbleven in juli 2025
Geverifieerde beoordeling
10/10 – Voortreffelijk
Matt H.
17 aug 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Great Experience
House was spacious, clean, and exactly as described in the listings. We had a great time!
7 nachten verbleven in juli 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
Susan P.
20 okt 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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!
3 nachten verbleven in oktober 2025
Geverifieerde beoordeling
10/10 – Voortreffelijk
Liz W.
1 aug 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
5 nachten verbleven in juli 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
Jen D.
8 jan 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
3 nachten verbleven in december 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
Hillery Y.
28 jan 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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!
3 nachten verbleven in januari 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
Anne J.
2 mei 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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!
3 nachten verbleven in april 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
kim d.
22 feb 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
5 nachten verbleven in februari 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
Deanna R.
1 apr 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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!
4 nachten verbleven in maart 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
Lynn B.
19 sep 2022
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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!!
4 nachten verbleven in september 2022
Geverifieerde beoordeling
10/10 – Voortreffelijk
Dee Dee
29 jul 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
7 nachten verbleven in juli 2023
Geverifieerde beoordeling
8/10 – Goed
Joanne Y.
16 jun 2024
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
4 nachten verbleven in juni 2024
Geverifieerde beoordeling
10/10 – Voortreffelijk
helen w.
9 jul 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
7 nachten verbleven in juni 2025
Geverifieerde beoordeling
10/10 – Voortreffelijk
Kimberly T.
25 jun 2026
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
6 nachten verbleven in juni 2026
Geverifieerde beoordeling
10/10 – Voortreffelijk
Matt K.
30 mrt 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
7 nachten verbleven in maart 2025
Geverifieerde beoordeling
10/10 – Voortreffelijk
Brian H.
18 apr 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
3 nachten verbleven in april 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
Robert G.
9 apr 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
7 nachten verbleven in april 2023
Geverifieerde beoordeling
10/10 – Voortreffelijk
Rachel B.
23 aug 2023
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.