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!!!
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.
Matt K.
2025 年 3 月に 7 泊滞在
10/10 (非常に良い)
robert r.
2024 年 11 月 14 日
良かった点 : 清潔度
Friends weekend
Perfect large space on a quiet and pretty area. Really great space.
robert r.
2024 年 11 月に 4 泊滞在
10/10 (非常に良い)
Matt H.
2024 年 8 月 17 日
良かった点 : 清潔度
Great Experience
House was spacious, clean, and exactly as described in the listings. We had a great time!
Matt H.
2024 年 7 月に 7 泊滞在
10/10 (非常に良い)
Adam H.
2024 年 8 月 4 日
良かった点 : 清潔度
Reunion
Great stay
Adam H.
2024 年 7 月に 4 泊滞在
8/10 (良い)
Joanne Y.
2024 年 6 月 16 日
良かった点 : 清潔度
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.
Joanne Y.
2024 年 6 月に 4 泊滞在
10/10 (非常に良い)
Richard S.
2024 年 4 月 27 日
良かった点 : 清潔度
Great long weekend
Host and property were great
Richard S.
2024 年 4 月に 4 泊滞在
10/10 (非常に良い)
Deanna R.
2024 年 4 月 1 日
良かった点 : 清潔度
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!
Deanna R.
2024 年 3 月に 4 泊滞在
10/10 (非常に良い)
Hillery Y.、Bowie, Maryland
2024 年 1 月 28 日
良かった点 : 清潔度
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!
Hillery Y.
2024 年 1 月に 3 泊滞在
10/10 (非常に良い)
Jen D.
2024 年 1 月 8 日
良かった点 : 清潔度
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.
Jen D.
2023 年 12 月に 3 泊滞在
10/10 (非常に良い)
Sandra L.
2023 年 10 月 17 日
良かった点 : 清潔度
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!
Sandra L.
2023 年 10 月に 10 泊滞在
10/10 (非常に良い)
Kevin R.
2023 年 9 月 10 日
良かった点 : 清潔度
Family getaway
Perfect spot for families with little kids. Great host and beautiful home.
Kevin R.
2023 年 8 月に 3 泊滞在
10/10 (非常に良い)
Rachel B.
2023 年 8 月 23 日
良かった点 : 清潔度
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.
Rachel B.
2023 年 8 月に 7 泊滞在
10/10 (非常に良い)
Liz W.
2023 年 8 月 1 日
良かった点 : 清潔度
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.
Liz W.
2023 年 7 月に 5 泊滞在
10/10 (非常に良い)
Dee Dee
2023 年 7 月 29 日
良かった点 : 清潔度
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.
Dee Dee
2023 年 7 月に 7 泊滞在
10/10 (非常に良い)
Daniel S.
2023 年 7 月 11 日
良かった点 : 清潔度
Wonderful Family House
This is a wonderful property for bigger families. It has plenty to do for all ages.
Daniel S.
2023 年 6 月に 7 泊滞在
10/10 (非常に良い)
Anne J.
2023 年 5 月 2 日
良かった点 : 清潔度
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!
Anne J.
2023 年 4 月に 3 泊滞在
10/10 (非常に良い)
Sarah C.
2023 年 4 月 25 日
良かった点 : 清潔度
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.
Sarah C.
2023 年 4 月に 4 泊滞在
10/10 (非常に良い)
Brian H.
2023 年 4 月 18 日
良かった点 : 清潔度
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.
Brian H.
2023 年 4 月に 3 泊滞在
10/10 (非常に良い)
Robert G.
2023 年 4 月 9 日
良かった点 : 清潔度
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.
Robert G.
2023 年 4 月に 7 泊滞在
10/10 (非常に良い)
kim d.
2023 年 2 月 22 日
良かった点 : 清潔度
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.
kim d.
2023 年 2 月に 5 泊滞在
10/10 (非常に良い)
Cheryl T.
2022 年 10 月 21 日
良かった点 : 清潔度
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.
Cheryl T.
2022 年 10 月に 5 泊滞在
10/10 (非常に良い)
Lynn B.
2022 年 9 月 19 日
良かった点 : 清潔度
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!!
Lynn B.
2022 年 9 月に 4 泊滞在
10/10 (非常に良い)
Robin T.
2022 年 8 月 27 日
良かった点 : 清潔度
Gorgeous and relaxing
This is a beautiful home with an amazing view that has everything you could want for a restful vacation.
Robin T.
2022 年 8 月に 7 泊滞在
10/10 (非常に良い)
John C.
2022 年 8 月 3 日
良かった点 : 清潔度
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.
John C.
2022 年 7 月に 14 泊滞在
10/10 (非常に良い)
Sandi C.、Washington, DC
2022 年 7 月 12 日
良かった点 : 清潔度
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.