Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS) Reviews, Deals & Photos 2025

Q: Does Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS) have a pool?

Yes, this property has an outdoor pool.

Q: Is Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS) pet-friendly?

Yes, this property allows cats and dogs (limit 1 total).

Q: Where is Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS) located?

Located on the waterfront, this family-friendly holiday home is within 9 mi (15 km) of Oxford Museum, Chesapeake Bay Maritime Museum and Saint Michaels Village. Saint Marys Square and Church Cove Park are also within 9 miles (15 km).

10/10 Excellent

Christine P.

29 May 2025

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

MDW Stay at Deep Neck Point

This property is even prettier in person!! We have a huge extended family and there was plenty of space for everyone. The host and property manager both made themselves available to answer any questions and responded very quickly. Excellent trip - we would love to stay again in the future!

Stayed 3 nights in May 2025

10/10 Excellent

Lawrence G.

29 Sept 2024

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

Fabulous property!

This is a wonderfully appointed property with loads of fun activities for adults and children alike.

Stayed 3 nights in Sep 2024

10/10 Excellent

B. P.

29 Nov 2023

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

Great spot

Great family spot!

Stayed 4 nights in Nov 2023

10/10 Excellent

michael c., Annapolis ,Maryland

6 Jun 2022

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

Outstanding Property

It was a wonderful experience and such a beautiful property.

Stayed 2 nights in May 2022

10/10 Excellent

Amanda K.

15 Apr 2024

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

Exquisite Family Estate - Extraordinary Experience

This is a magnificent property; lovingly curated and impeccably decorated while equipped with every thoughtful consideration for practical use. We could not have dreamt of a more wonderful place to gather and celebrate family. Only serious, considerate guests should inquire - this is a very special place.

Stayed 2 nights in Apr 2024

10/10 Excellent

Rakesh C., Arlington, VA

2 Apr 2021

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

Excellent Property

Can't say enough good things about this property. Tons of stuff to do, layout is great for large groups. Owner is very responsive. Would highly recommend.

Stayed 3 nights in Mar 2021

10/10 Excellent

Tracy M.

13 Aug 2024

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

Beautiful Property

We were a family of 11, infant to senior. This property is amazing and basically a mini resort for a family even larger than ours. The pool was a huge hit with all ages, Edie silly given the unusually warm weather. The tennis court was used, the ping pong table, lots of fishing and crabbing off the dock, hammock time and of course sitting in the chairs on the porch for morning coffee, dinner for all on the expensive patio and watching the sunsets from the many seating areas along the water. It was a fabulous stay.

Stayed 7 nights in Aug 2024

10/10 Excellent

Beth G.

5 Aug 2023

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

Staying at Deep Neck Point

The house and the grounds are amazing! We particularly liked sitting on the back veranda on rockers looking at the bay —especially at sunset. The kids loved the pool, fishing from the dock, the zip line and just playing outside on the grounds. There was plenty of room to accommodate our family of 9.

Stayed 7 nights in Jul 2023

10/10 Excellent

Vilma B.

21 Sept 2020

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

Home vacation.

Very very nice, recommend highly. Will return.

Stayed 3 nights in Sep 2020

8/10 Good

Brian C.

1 Jul 2024

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

Eastern Shore

Spectacular spot and beautiful house with all the amenities. Freezer wasn’t working and an unexpected extra cleaning charge were the only caveats.

Stayed 3 nights in Jun 2024

10/10 Excellent

Robert N.

6 Sept 2020

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

Perfect Getaway

The listing speaks for itself...a fully stocked home on the water with plenty for adults and children to stay entertained. Pool, tennis, crabbing, fishing, board games, etc. William our host was incredibly kind and accessible to answer any questions we had and make sure we had an enjoyable stay. Definitely hope to return soon!

Stayed 5 nights in Aug 2020

10/10 Excellent

Sonia D.

9 May 2024

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

Great location

We enjoyed the time there. Especially the backyard. Although the weather did not cooperate on Saturday. There could be some improvements on maintenance of the master shower. It was clogged, eeek. We only found one hairdryer in the house. Overall cool experience.

Stayed 2 nights in Apr 2024

10/10 Excellent

Sharon S.

3 Jun 2019

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

Beautiful and luxurious retreat on the Chesapeake

The owner’s well-appointed personal vacation home was stately, well-maintained and comfortable, with every fun activity and convenience you might dream about. My parents, sisters and our kids had plenty of room, both inside and outside, to be altogether, to break into smaller groups, and to assure privacy. The additional kitchens meant we could cook, garden, and enjoy poolside snacks all at the same time. Perfect 10+++++

Stayed 2 nights in May 2019

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Patricia P.

28 Dec 2014

Unbelievable Vacation Retreat

The house & property were even more beautiful in person. The house was immaculate & very well stocked. Location was unbelievable with incredible waterfront views & memorable evening sunsets. The dock, pool, pool house & extensive lawn provided many happy hours of entertainment. The town of St. Michael's is lovely but mostly we stayed at the house as no one wanted to leave. The owner & caretaker were very accommodating. My children & grandchildren said it was the best vacation ever. Would highly recommend. Hope to return.

10/10 Excellent

Laurie M.

4 Aug 2024

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

Amazing Vacation

My husband and I have brought our 9 family members (adult children and grandchildren) to the Eastern Shore quite a few times, and stayed in large homes, but Royal Oak is by far the nicest home where we have stayed. It is like a resort, inside and out. The views are spectacular, and the grounds are just beautiful. Outside we played tennis, basketball, and volleyball, and went swimming, crabbing and biking! We ran out of time before we got to kayaking! Inside there were 2 dishwashers and refrigerators! And there was a washer/dryer on each floor! The furnishings were just beautiful! The kitchen was well appointed and had everything you might need! I could go on and on. But suffice it to say that Royal Oak provided the beauty and the amenities for a memorable vacation!

Stayed 7 nights in Jul 2024

10/10 Excellent

Debbie R.

28 Oct 2023

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

THE place for a "friends and family" weekend!

The house and the property looked great online. But how often does it actually look (and feel) better in person? This property is even better than the pictures. Fifteen of us gathered for the weekend (to pay tribute to a friend who had passed away). Folks came in from all over (Switzerland, Martha's Vineyard, LA, etc.) These folks are no stranger to great settings with great views. And their reaction to Deep Neck Point was one word. Wow. Why wow? Was it the lightning fast wi-fi? While the property does have wi-fi, be prepared for a weekend where your face is not buried in your phone. We walked the property with 3,000 feet of water frontage. We discovered not one, but two stone fire pits (with wood stacked close by). We threw pass patterns on the hundreds and hundreds of yards of perfectly mowed grass. No rotator cuff or hamstring injuries to report. The kids (and some adults) spent hours on the zipline that zooms right over the water. Others played inside, making full use of the foosball table, air hockey, billiards table...and thanks to an ample supply of AA batteries, we also played some Wii bowling and boxing. All of this activity made for some hungry and thirsty residents. The giant kitchen (with 2 dishwashers) and two large dining tables fit us all comfortably. And the stocked "pay it forward" bar cart was another noble feature. To a person, everyone remarked..."when can we come back?" Thank you for opening up your home for our memorable weekend gathering.

Stayed 3 nights in Oct 2023

10/10 Excellent

Kelly M., Conneticut, New Jersey, Maryland, West Virginia, Florida

9 Jul 2022

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

Extended family annual vacation

Our family has been renting properties on the eastern shore annually for over 30 years. Our extended family is quite large, consisting of grandparents, parents, children, grandchildren, aunts and uncles. Most of the family do not stay the entire week, so we have people arriving and departing throughout the week. The largest number staying at one time has been up to 24 people. Most rental properties are not large enough, so we always had people sleeping on air mattresses and couches. This was the first time in thirty years that everyone actually had a bed to sleep in, a seat at the table to eat, and a place to park their car. The house and property had something for everyone between the pool, waterfront dock, zipline, tennis court, basketball court, volley ball net, as well as a quiet, traffic free neighborhood to walk, run, and bike in. There are plenty of bathrooms, the kitchen is very well equipped for creating large family meals, and there is enough seating for everyone to enjoy meals together. The outside space is also very well equipped with seating for everyone to enjoy the fire pit, water view, and family games in the yard. This was the first time we decided to rent somewhere other than the Maryland/Delaware shore b/c the houses at the shore are never large enough, so we pay a whole lot of money for everyone to basically be inconvenienced. That was never really a problem when we were younger, but as we have gotten older, sleeping on air mattresses and couches are just not fun. This house had so much to offer that we did not even miss the beach, and we most certainly did not miss the crazy beach traffic and overcrowded grocery stores, restaurants, and shopping areas that have become the norm at the eastern shore. I highly recommend this property!!

Stayed 7 nights in Jul 2022

10/10 Excellent

Eliza S.

6 Oct 2024

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

Perfectly Beautiful

Wonderfully comfortable house and idyllic setting — plus all the amenities (and then some). Perfect setting for our get together with friends.

Stayed 2 nights in Oct 2024

10/10 Excellent

Rebecca W.

20 Aug 2023

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

Making Memories - First Class Vacation

One word - phenomenal! I want to first say the communication with the property owner was top notch! We couldn’t have asked for a better week. The home is beautiful with plenty for the entire crew to do. Everyone enjoyed the expansive pool - it is large enough for diving competitions, marco polo and basketball…happening all at once! The water views were spectacular from every angle of the property. The home was very well appointed with everything you can possibly think of - but most of our time was spent outside, either riding bikes, walking the breathtaking property, playing basketball, volleyball, pickleball or tennis! Oh wait how can I forget the private beach area and dock! This property has it all! If you want to stay in you can enjoy one of the many smart TVs, board games, books and chef’s kitchen. If you prefer outdoor space - it has it all including a dock where you can dock a boat, crab and fish! My family had one of the best vacations! Thank you Deep Neck Point family for sharing your beautiful and unforgettable property. We would definitely return!

Stayed 7 nights in Aug 2023

10/10 Excellent

Rakesh C., Arlington, VA

26 Oct 2022

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

Phenomenal Property for small/large groups

Love this place. Host is excellent and very responsive. Tons of activities to do here anytime of the year. Would highly recommend.

Stayed 3 nights in Oct 2022

10/10 Excellent

Hannah K.

18 Oct 2022

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

Lovely place

We had a lovely time! Wished we could have stayed longer. This place had everything you could need and want for a fun vacation with kids! Thanks again!

Stayed 2 nights in Sep 2022

10/10 Excellent

Jodie K.

6 Oct 2022

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

Perfect spot for a family get-together

We loved this property as a perfect hub to celebrate a 90th birthday. Conveniently located between Easton and St Michael's, this house had plenty of space to get together or to branch off. Highly recommend!

Stayed 3 nights in Sep 2022

10/10 Excellent

Kathy B.

23 Sept 2022

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

View is worth it

Great place for family getaway. Loved the bikes, tennis and pool. Just sitting on the porch watching the sunset or by the fire pit, was so nice and relaxing. Wonderful stay

Stayed 4 nights in Sep 2022

10/10 Excellent

Joyce and Naftali S.

6 Sept 2022

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

Perfect Getaway for Our Crew: Ages 1 1/2 to 72

We spent a magical week at Deep Neck Point with all 3 generations of our family. There was something for everyone! We all enjoyed the beautiful pool (with its convenient pool house, many toys and a ping pong table in the shade). The big kids had a blast on the zipline. The little ones were thrilled to pick their own cherry tomatoes from the garden (approved by the owner!). The full tennis and volleyball courts, the fire pit, and indoor game room added to our enjoyment. The house and property are beautiful; as is the spectacular sunset every evening over Chesapeake Bay. We spent two lovely evenings in the charming town of St. Michaels. We want to thank Will, the owner, for being extremely responsive to our questions and requests.

Stayed 6 nights in Aug 2022

10/10 Excellent

Carol D.

23 Aug 2022

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

2022 Family Vacation

The house and property are wonderful! It was very hot so we didn’t have an opportunity to use everything. We said we could have held a mini family Olympics with all the outside provided! We hope to return when it’s a little cooler! My family loved it!

Stayed 7 nights in Aug 2022

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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

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