Onsite parking is available at the property.

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND Reviews, Deals & Photos 2025

Q: Does Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Q: Is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND pet-friendly?

No, pets are not allowed at this property.

Q: Where is Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND located?

This family-friendly Sherwood vacation home is located on the waterfront, within 3 mi (5 km) of Knapp's Narrows Marina & Inn, Phillips Wharf Environmental Center and Back Creek Community Park. Goat Island and Kronsberg Park are also within 3 mi (5 km).

10/10 Excellent

James S.

6 August 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!

Stayed 9 nights in Jul 2025

10/10 Excellent

Adam H.

4 August 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Reunion

Great stay

Stayed 4 nights in Jul 2024

10/10 Excellent

Richard S.

27 April 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great long weekend

Host and property were great

Stayed 4 nights in Apr 2024

10/10 Excellent

helen w.

9 July 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.

Stayed 7 nights in Jun 2025

10/10 Excellent

robert r.

14 November 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends weekend

Perfect large space on a quiet and pretty area. Really great space.

Stayed 4 nights in Nov 2024

10/10 Excellent

Kevin R.

10 September 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family getaway

Perfect spot for families with little kids. Great host and beautiful home.

Stayed 3 nights in Aug 2023

10/10 Excellent

Daniel S.

11 July 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.

Stayed 7 nights in Jun 2023

10/10 Excellent

Robin T.

27 August 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.

Stayed 7 nights in Aug 2022

10/10 Excellent

Matt H.

17 August 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!

Stayed 7 nights in Jul 2024

10/10 Excellent

Liz W.

1 August 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.

Stayed 5 nights in Jul 2023

10/10 Excellent

Margery L.

11 September 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.

Stayed 5 nights in Sep 2021

10/10 Excellent

Jen D.

8 January 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.

Stayed 3 nights in Dec 2023

10/10 Excellent

kim d.

22 February 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.

Stayed 5 nights in Feb 2023

10/10 Excellent

Hillery Y., Bowie, Maryland

28 January 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!

Stayed 3 nights in Jan 2024

10/10 Excellent

Matt K.

30 March 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.

Stayed 7 nights in Mar 2025

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!

Stayed 3 nights in Apr 2023

10/10 Excellent

Deanna R.

1 April 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!

Stayed 4 nights in Mar 2024

8/10 Good

Joanne Y.

16 June 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.

Stayed 4 nights in Jun 2024

10/10 Excellent

Dee Dee

29 July 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.

Stayed 7 nights in Jul 2023

10/10 Excellent

Brian H.

18 April 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.

Stayed 3 nights in Apr 2023

10/10 Excellent

Robert G.

9 April 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.

Stayed 7 nights in Apr 2023

10/10 Excellent

Rachel B.

23 August 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.

Stayed 7 nights in Aug 2023

10/10 Excellent

Sandi C., Washington, DC

12 July 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Sarah C.

25 April 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Sandra L.

17 October 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!

Stayed 10 nights in Oct 2023

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

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