Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on the private dock to evening swims under pastel skies, this home blends Chesapeake Bay charm with resort-style amenities. Designed for families and friends, every space invites connection, comfort, and unforgettable memories.
Talbot County Licensure: STN-25-10
The Space:
At the end of a quiet road, where trees give way to endless water, you’ll find Overlook Farm — a luxurious waterfront retreat made for connection and calm. The open-concept layout flows from a chef’s kitchen with an oversized island into inviting dining areas indoors and out. Multiple living spaces offer room to gather or spread out, while a game room sparks friendly competition and tucked-away nooks invite a good book. Four serene bedrooms each frame a private view of the water, bringing golden sunrises and gentle evening breezes to your stay. Outside, the private pool, sun loungers, and shaded seating create the perfect setting for long, lingering days on the shore.
What you’ll love:
- Unmatched waterfront views from every bedroom
- Chef’s kitchen with oversized island & premium appliances
- Multiple living rooms & cozy nooks for relaxation or play
- Game room for friendly competition & late-night laughter
- Private pool overlooking the bay with loungers & dining space
- Indoor & outdoor dining areas for memorable meals
- Quiet corners perfect for reading, journaling, or reflection
- Spacious lawn & gathering areas for sunrise coffee or sunset drinks
Overlook Farm is more than a home — it’s a place for reconnection, restoration, and creating lasting memories.
Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.
Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.
The Neighborhood:
Rural waterfront, peaceful and private.
Getting Around:
Centrally located between downtown Easton and historic St Michaels.
Other Things to Note:
We provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays. Personal care items are not supplied and must be brought by guests. We can welcome your furry friend for a nonrefundable pet fee of $200.
The private pool is scheduled to open for the season by Memorial Day.
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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
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Royal Oak
Located in Royal Oak, this holiday home is on the waterfront. St. Michaels Museum and Avalon Theatre are local landmarks, and some of the area's activities can be experienced at St. Michaels Winery and Windon Distilling. Travelling with kids? Consider Chesapeake Bay Maritime Museum and Easton Cycle and Sport. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling.
Chesapeake Bay Maritime Museum - 22 min drive - 17.7 km
Getting around
Cambridge Station - 48 min drive
Easton, MD (ESN-Easton - Newnam) - 22 min drive
Restaurants
Doc's Sunset Grille - 38 min drive
t at The General Store - 11 min drive
Blue Heron Coffee - 18 min drive
Rise Up Coffee - 16 min drive
Rusticana (St. Michael's) - 17 min drive
Frequently asked questions
Does Waterfront Paradise | Pool, Views & Serenity have a pool?
Yes, this property has a pool.
How much does it cost to stay at Waterfront Paradise | Pool, Views & Serenity?
As of 9 May 2026, prices found for a 1-night stay for 2 adults at Waterfront Paradise | Pool, Views & Serenity on 30 August 2026 start from NZ$1,173, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Waterfront Paradise | Pool, Views & Serenity pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Waterfront Paradise | Pool, Views & Serenity?
On-site parking is available at the property.
What time is check-in at Waterfront Paradise | Pool, Views & Serenity?
Check-in begins at 4:00 PM.
What time is check-out at Waterfront Paradise | Pool, Views & Serenity?
Checkout is at 10:00 AM.
Where is Waterfront Paradise | Pool, Views & Serenity located?
Located on the waterfront, this family-friendly holiday home is within 9 mi (15 km) of Saint Michaels Village, Chesapeake Bay Maritime Museum and Saint Marys Square. Church Cove Park and Back Creek Park are also within 9 miles (15 km).
About the host
Hosted by Jennifer Brown
Languages:
English
Premier Host
They consistently provide great experiences for their guests