This vacation home is located 5.6 mi (9 km) from Oxford Museum and 7.8 mi (12.6 km) from Saint Michaels Village. The vacation home includes a private pool, a kitchen, and a fireplace.
Chesapeake Bay Maritime Museum - 25 min drive - 11.1 miles
1879 Hooper Straight Lighthouse - 25 min drive - 11.1 miles
Getting around
Cambridge Station - 49 min drive
Easton, MD (ESN-Easton - Newnam) - 29 min drive
Restaurants
Foxy's - 21 min drive
Chesapeake Landing Restaurant - 25 min drive
The Blue Crab - 21 min drive
Carpenter Street Saloon - 21 min drive
The Crab Claw - 21 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 12 adults. Located on a private 60 acre peninsula that reaches out into a mile-wide stretch of Broad Creek, the 8,000 square foot house is surrounded by 270 ° of water. The property, which was built in 2003, features a large in-ground pool, a 150 foot dock with 4 ft of water at the end of the dock, a tennis court, a volley ball court, a full basket ball court, a 200 foot zip line over a marsh, a game room with a pool table, a ping pong table, a fire pit with seating for 12, and a small kids playground.
Moreover, the property is located on a secluded 60 acre parcel that is ideal for nature hikes, sports, hunting (in season), and fishing. Guests may dock their own boat at our dock, or may arrange for local fishing guides to pick them up to take advantage of the rich fishing options of the Chesapeake Bay.
This house is perfect for family retreats. We designed it such that there is no reason to leave, but if you do, there is tons to do.
Description of House: The house was custom built in 2003 by a renowned local builder and the interior was designed by an accomplished interior designer. Much of the furniture was sourced from local antique stores and auctions.
The 1st floor features ~a large eat-in kitchen with a refrigerator/freezer, double oven and 2 dishwashers ~a utility room with refrigerator and washer/dryer, a casual dining room that seats 12 ~a formal dining room that seats 8 ~a private office ~a large living room with four sofas a flat panel TV/VCR/DVD and seating for 14, ~a wood paneled study with flat screen TV/VCR/DVD and Wii plus seating for 6 ~2 bedrooms and 2.5 bath rooms. ~a 2000 s.f. wrap around porch
The second floor includes: ~game room with pool table, foosball table, TV and VCR/DVD ~4 bed rooms and 3 full bathrooms. The master bedroom has a porch overlooking the water. The bedrooms include: BR2 (twin beds with private bath), BR3 (full bed with private bath), BR4 (twin beds, no bath/shared bath with MBR of BR2).
The third floor: ~storage area plus access to a roof top crows nest. Half bath.
Exterior: The house is accessible by a private gravel drive that opens into a 60 acre private oasis.
The home sits on a manicured 5 acre lot with plenty of room to play football, lacrosse, baseball and other activities. A full sized basketball court with two 10' adjustable hoops sits adjacent to the house and serves as an overflow parking area. In the back yard, which overlooks the water, a 200 foot zip-line runs over a waterfront marsh, adjacent to a large fire pit that is surrounded by 10 Adirondack chairs and tables. The fire pit is perfect for making s'mores or just relaxing and watching the sun set off the edge of the property.
A full sized fenced in tennis court sits within 200 feet of the house, and a large fenced-in pool (not heated -- available April 15 - October 15) with pool house, ping pong table and 10 lounge chairs as well as 2 dining tables and 2 picnic tables. A shaded hammock is perfect for the summer months.
Next to the tennis court is a full sized grass volleyball/badminton court. Rackets and most equipment is provided. We have cornhole and spike ball in the pool house.
Hunters will enjoy the 2 waterfront duck blinds and 3 inland goose blinds, along with acres of woods for exploring. Note - duck blinds get booked early and require a guide. Please contact owner for additional details.
St. Michaels, Easton and Oxford-Belleview Ferry: Locally, you are 15 minutes (9 miles) away from the quaint town of St. Michaels. There you will find 5 star restaurants and spas, ice cream parlors, the world-class Chesapeake Bay Maritime Museum and numerous boutiques for great antiquing and shopping.
Just 20 minutes from the house is Easton, MD, the county seat. Easton features top notch art galleries and more 5 star restaurants.
And all guests are encouraged to bring bikes to take the 6 mile ride to the Oxford-Belleview Ferry. Established in 1683, it is the oldest continually operating ferry in North America. Today it takes cars and bikes on a 10 minute ride across the Tred Avon river from Belleview, MD to Oxford, MD and back. In Oxford you will find more great restaurants and shops along with world-class sailing.
All reservations are subject to owner screening and approval before they become final. This will occur within 24 hours of the booking.
The vacation home is air-conditioned and features a kitchen, 6.5 bathrooms, and a balcony. There's space to spread out with 6 bedrooms and a dining area. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a private pool, a washer/dryer, and a fireplace. Housekeeping is available on request.
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
Bicycles
Garden
Housekeeping (on request)
Unit size: 8,000 square feet
Policies
Check-in
Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 30
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Check-out instructions
The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights
When you are ready to depart, please leave any bed you used unmade so that the cleaning crew knows to strip and change it. There is no need to strip it or start laundry yourselves.
Place all used towels in the bathroom(s) on the floor
Please remove all food that you cooked or brought with you from the refrigerator. Please take out all trash. Remember, all trash must be bagged,
Pets
This property welcomes pets
Dogs and cats only
1 total pets
Service animals exempt from fees
Note from host: Adult dogs/cats only. No puppies or kittens.
Important information
You need to know
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Check-in: 3:00 PM
Check-out: 10:00 AM
Minimum check-in age: 30
Property Registration Number ST-660-MCK
We should mention
Details about charges, deposits, or other important information:
This property is managed by a private host, not a professional engaged in trade or business.
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.
Property is also known as
Luxurious Extremely Private Waterfront Estate House Royal Oak
Luxurious Extremely Private Waterfront Estate Royal Oak
Luxurious Extremely Private Waterfront Estate
Luxurious and Extremely Private Waterfront Estate Royal Oak
Luxurious Extremely Private Waterfront Estate House
Luxurious Extremely Private Waterfront Estate
Frequently asked questions
What is there to do close to this vacation home?
This vacation home is located in Royal Oak, close to Saint Michaels Village, St. Michaels Winery, and St. Michaels Marina. You'll also find Chesapeake Bay Maritime Museum and 1879 Hooper Straight Lighthouse nearby.
Will I be able to park at this vacation home?
Yes, there is a garage.
Is this vacation home next to a casino?
No, this vacation home is not connected to a casino.
Is there an indoor pool at this vacation home?
No, this vacation home doesn't have an indoor pool; however, there is an outdoor pool.
What do couples enjoy most about Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)?
This waterfront vacation home offers many amenities for couples such as a private pool, a fireplace, and access to a chef.
Are there hot tubs at Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)?
No, there isn't a spa tub at this vacation home.
Does this vacation home offer breakfast?
No, this vacation home doesn't offer breakfast.
Does this vacation home allow pets to stay for free?
Although cats and dogs can't stay for free, they are welcome at this vacation home.
Does this vacation home have connecting rooms?
No, this vacation home doesn't feature connecting guestrooms.
How close is the airport from this vacation home?
The closest major airport to this vacation home is Easton, MD (ESN-Easton - Newnam), which is 14.5 mi away (29 minutes by car).
Are there rooms with balconies that I can book at Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)?
Yes, every accommodation at Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS) comes with a balcony.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS) Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 86 out of 87 reviews
10 - Excellent
86
Rating 8 - Good. 1 out of 87 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 87 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 87 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 87 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
10/10 Excellent
Karl F.
Jun 16, 2025
Liked: Cleanliness
Outstanding
We hosted a family reunion on the eastern shore and could not have picked a better location. Spacious home, even more spacious grounds and plenty to keep everyone occupied: pool, tennis, basketball, kayaking, beach, hiking and lounging on the porch. Plenty of sleeping space for 8 adults, 6 kids and 2 infants. The “ kids dorm” on the top floor was a big hit! The owners treated us like personal guests with access to virtually everything in the house and on the property.Have rented several great properties through VRBO, this was the best.
Karl F.
Stayed 3 nights in Jun 2025
10/10 Excellent
janet b., Brookline, MA
Jun 5, 2025
Liked: Cleanliness
Royal Oaks Paradise
12 adults spent 5 days, 4 nights by the Chesapeake Bay.. eating, swimming, kayaking, biking and laughing in this incredibly well stocked, beautiful home. We loved it so much that we can’t wait to return!!
janet b.
Stayed 4 nights in Jun 2025
10/10 Excellent
Christine P.
May 29, 2025
Liked: Cleanliness
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!
Christine P.
Stayed 3 nights in May 2025
10/10 Excellent
Eliza S.
Oct 6, 2024
Liked: Cleanliness
Perfectly Beautiful
Wonderfully comfortable house and idyllic setting — plus all the amenities (and then some). Perfect setting for our get together with friends.
Eliza S.
Stayed 2 nights in Oct 2024
10/10 Excellent
Lawrence G.
Sep 29, 2024
Liked: Cleanliness
Fabulous property!
This is a wonderfully appointed property with loads of fun activities for adults and children alike.
Lawrence G.
Stayed 3 nights in Sep 2024
10/10 Excellent
Tracy M.
Aug 13, 2024
Liked: Cleanliness
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.
Tracy M.
Stayed 7 nights in Aug 2024
10/10 Excellent
Laurie M.
Aug 4, 2024
Liked: Cleanliness
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!
Laurie M.
Stayed 7 nights in Jul 2024
8/10 Good
Brian C.
Jul 1, 2024
Liked: Cleanliness
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.
Brian C.
Stayed 3 nights in Jun 2024
10/10 Excellent
Sonia D.
May 9, 2024
Liked: Cleanliness
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.
Sonia D.
Stayed 2 nights in Apr 2024
10/10 Excellent
Amanda K., Kirkland, WA, USA
Apr 15, 2024
Liked: Cleanliness
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.
Amanda K.
Stayed 2 nights in Apr 2024
10/10 Excellent
B. P.
Nov 29, 2023
Liked: Cleanliness
Great spot
Great family spot!
B. P.
Stayed 4 nights in Nov 2023
10/10 Excellent
Debbie R.
Oct 28, 2023
Liked: Cleanliness
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.
Debbie R.
Stayed 3 nights in Oct 2023
10/10 Excellent
Rebecca W.
Aug 20, 2023
Liked: Cleanliness
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!
Rebecca W.
Stayed 7 nights in Aug 2023
10/10 Excellent
Beth G.
Aug 5, 2023
Liked: Cleanliness
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.
Beth G.
Stayed 7 nights in Jul 2023
10/10 Excellent
Rakesh C., Arlington, VA
Oct 26, 2022
Liked: Cleanliness
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.
Rakesh C.
Stayed 3 nights in Oct 2022
10/10 Excellent
Hannah K.
Oct 18, 2022
Liked: Cleanliness
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!
Hannah K.
Stayed 2 nights in Sep 2022
10/10 Excellent
Jodie K.
Oct 6, 2022
Liked: Cleanliness
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!
Jodie K.
Stayed 3 nights in Sep 2022
10/10 Excellent
Kathy B.
Sep 23, 2022
Liked: Cleanliness
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
Kathy B.
Stayed 4 nights in Sep 2022
10/10 Excellent
Joyce and Naftali S.
Sep 6, 2022
Liked: Cleanliness
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.
Joyce and Naftali S.
Stayed 6 nights in Aug 2022
10/10 Excellent
Carol D.
Aug 23, 2022
Liked: Cleanliness
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!
Carol D.
Stayed 7 nights in Aug 2022
10/10 Excellent
Mary D.
Aug 21, 2022
Liked: Cleanliness
Deep Neck Point was perfect for our family
This was the first time we chose a family gathering on the Eastern Shore rather than the Outer Banks, and we couldn’t be happier with the house, the location, and our hosts. We had great little day trips to picturesque waterfront towns, and on some days just stayed on the property enjoying all that it had to offer from the pool to zip line, Pickleball, etc. Watching the sun set from the rocking chairs on the back porch was a daily must, allowing the three generations to reconnect and discuss the day’s activities. The public rooms fit all 12 of us comfortably, and also allowed the youngest to break off and spend some screen time while others chatted. Thanks to our hosts for sharing this wonderful compound! They were responsive to our questions beforehand and provided great tips for family friendly restaurants.
Mary D.
Stayed 7 nights in Aug 2022
10/10 Excellent
Jan C.
Jul 19, 2022
Liked: Cleanliness
Enjoyed by 3 generations
This property has it all! We were a family with ages from 7 to 70 and everyone of us truly enjoyed ourselves. The house and surroundings are amazing! Will has thought of everything and we thank him for sharing this special place with us!
Jan C.
Stayed 7 nights in Jun 2022
10/10 Excellent
Kelly M., Conneticut, New Jersey, Maryland, West Virginia, Florida
Jul 9, 2022
Liked: Cleanliness
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!!
Kelly M.
Stayed 7 nights in Jul 2022
10/10 Excellent
michael c., Annapolis ,Maryland
Jun 6, 2022
Liked: Cleanliness
Outstanding Property
It was a wonderful experience and such a beautiful property.
michael c.
Stayed 2 nights in May 2022
10/10 Excellent
Lana Y., McLean, fairfax county
Apr 26, 2022
Liked: Cleanliness
Short and sweet.
The house was amazing!! The views, privacy, cleanliness, communication with Will, the whole experience was beyond expectations. The house is generously stocked with everything and we felt like we were in our own home. Easton is close enough for an outing. The fire pit and kayaks were awesome. Can’t wait to go back .