Title: Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=6034722&destination=Sherwood%2C+Maryland%2C+United+States+of+America&selected=64567851&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) 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 ![Golf - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/f3ee6fc0.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Sun-loungers, beach towels - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/a8374ca7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/4b373998.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/bcf1512f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND (Sherwood)](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/a7c6934a.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Welcome to TREMEZZO STAY - CHEASAPEAKE MANSION, the premier Eastern Shore destination in St. Michaels, MD. This luxurious 12,000 sqft home offers a heated pool from mid-March to mid-October and sits on 30 private acres with plenty of space for relaxation and play. ## Reviews 10 Exceptional ### Entire home 8 bedrooms9 bathroomsSleeps 1212000 sq ft ## Popular amenities - Kitchen - Washing machine - Dryer - Air-conditioning ## Add dates for prices Check-in Check-out Travellers ## 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 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 - 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. - 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 - At least 80% lighting from LEDs - Bicycles - Garden - Housekeeping (on request) - Local artist showcase - Locally-owned and organised tours and activities - Unit size: 12,000 square feet ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24700/24651/0ce19377.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Royal Sonesta Harbor Court Baltimore Otterbein - Pool - Hot tub - Spa - Pet-friendly 8.8 Excellent 1,807 reviews £117 includes taxes & fees 5 Apr - 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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 This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking. 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 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 ### 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 ## 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching. [Visit our Sherwood travel guide](https://www.expedia.co.uk/Sherwood.dx6034722) [View more Holiday homes in Sherwood](https://www.expedia.co.uk/Sherwood-Private-Holiday-Homes.d6034722-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C38.74462%2C-76.33889&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=VThvFmwAxiEWggvaACQelPsDn10=) Sherwood, MD ### 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 - Bridge Restaurant 6 min drive ## Frequently asked questions ### Does Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND have a pool? ### Is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND pet-friendly? ### How much is parking at Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND? ### Where is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.co.uk/lp/b/content-guidelines) 10 - Excellent 36 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 9.8 Location ## Reviews Verified ### 10/10 Excellent #### Kevin R. 10 Sept 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Family getaway Perfect spot for families with little kids. Great host and beautiful home. ##### Kevin R. Stayed 3 nights in Aug 2023 Verified ### 10/10 Excellent #### robert r. 14 Nov 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Friends weekend Perfect large space on a quiet and pretty area. Really great space. ##### robert r. Stayed 4 nights in Nov 2024 Verified ### 10/10 Excellent #### Jen D. 8 Jan 2024 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. ##### Jen D. Stayed 3 nights in Dec 2023 Verified ### 10/10 Excellent #### Hillery Y. 28 Jan 2024 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! ##### Hillery Y. Stayed 3 nights in Jan 2024 Verified ### 10/10 Excellent #### Deanna R. 1 Apr 2024 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! ##### Deanna R. Stayed 4 nights in Mar 2024 Verified ### 10/10 Excellent #### Dee Dee 29 Jul 2023 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. ##### Dee Dee Stayed 7 nights in Jul 2023 Verified ### 8/10 Good #### Joanne Y. 16 Jun 2024 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. ##### Joanne Y. Stayed 4 nights in Jun 2024 Verified ### 10/10 Excellent #### Matt K. 30 Mar 2025 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. ##### Matt K. Stayed 7 nights in Mar 2025 Verified ### 10/10 Excellent #### Rachel B. 23 Aug 2023 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. ##### Rachel B. Stayed 7 nights in Aug 2023 Verified ### 10/10 Excellent #### Sandra L. 17 Oct 2023 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! ##### Sandra L. Stayed 10 nights in Oct 2023 Verified ### 10/10 Excellent #### Ramin M. 22 Sept 2025 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. ##### Ramin M. Stayed 3 nights in Sep 2025 Verified ### 10/10 Excellent #### Susan P. 20 Oct 2025 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! ##### Susan P. Stayed 3 nights in Oct 2025 Verified ### 10/10 Excellent #### James S. 6 Aug 2025 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! ##### James S. Stayed 9 nights in Jul 2025 Verified ### 10/10 Excellent #### Adam H. 4 Aug 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Reunion Great stay ##### Adam H. Stayed 4 nights in Jul 2024 Verified ### 10/10 Excellent #### Richard S. 27 Apr 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great long weekend Host and property were great ##### Richard S. Stayed 4 nights in Apr 2024 Verified ### 10/10 Excellent #### Daniel S. 11 Jul 2023 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. ##### Daniel S. Stayed 7 nights in Jun 2023 Verified ### 10/10 Excellent #### Robin T. 27 Aug 2022 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. ##### Robin T. Stayed 7 nights in Aug 2022 Verified ### 10/10 Excellent #### Matt H. 17 Aug 2024 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! ##### Matt H. Stayed 7 nights in Jul 2024 Verified ### 10/10 Excellent #### Liz W. 1 Aug 2023 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. ##### Liz W. Stayed 5 nights in Jul 2023 Verified ### 10/10 Excellent #### Margery L. 11 Sept 2021 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. ##### Margery L. Stayed 5 nights in Sep 2021 Verified ### 10/10 Excellent #### helen w. 9 Jul 2025 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. ![](https://a.travel-assets.com/ugc/hotel-reviews/488aea5a-d7d0-421f-86be-549c7578dbd9-1752071150673.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/46642611-a85e-441a-a753-f970066d82a2-1752071150995.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### helen w. Stayed 7 nights in Jun 2025 Verified ### 10/10 Excellent #### kim d. 22 Feb 2023 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. ##### kim d. Stayed 5 nights in Feb 2023 Verified ### 10/10 Excellent #### Anne J. 2 May 2023 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! ##### Anne J. Stayed 3 nights in Apr 2023 Verified ### 10/10 Excellent #### Brian H. 18 Apr 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. Stayed 3 nights in Apr 2023 Verified ### 10/10 Excellent #### Robert G. 9 Apr 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. Stayed 7 nights in Apr 2023 ---