After booking the perfect St. Michaels, MD accommodations, make your Eastern Shore getaway extra special with one of our signature packages or romantic enhancements. As a top destination for Maryland getaways for couples, our hotel offers everything you need for a relaxing weekend escape. Advance notice is required for certain items, and availability is seasonal.
*Please note that our booking engine may display discounts differently than advertised. Sometimes it may split the savings across multiple nights or charges instead of showing the full discount in one place. Rest assured, you are still receiving the full value of the promotion.
The Suite Life
Indulge in luxury with The Suite Life package! Book a minimum of two nights in any of our suites and enjoy 25% off your last night. Experience the ultimate comfort and relaxation in our most elegant suites.
*For new reservations only. Offer cannot be combined with other offers. Blackout dates may apply.
Spontaneous Getaway
Feeling spontaneous? Book your Eastern Shore getaway the same week of your arrival and enjoy 20% off the last night of your stay! It’s the perfect way to escape for a quick, refreshing retreat.
*For new reservations only. Offer cannot be combined with other offers. Blackout dates may apply.
Stay a Little Longer
The longer you stay, the more you save! With our Stay a Little Longer package, enjoy 25% off the last night of your stay when you book 3 or more nights. It’s the perfect excuse to relax and enjoy an Eastern Shore getaway.
*For new reservations only. Offer cannot be combined with other offers. Blackout dates may apply.
Midweek Stay
Experience the magic of St. Michaels with our exclusive offer: enjoy 25% off the last night of your stay. Whether you’re seeking a cozy retreat or an adventurous escape, our luxurious accommodations provide the perfect setting for your next getaway. Book now to take advantage of this limited-time offer.
*For new reservations only. Offer cannot be combined with other offers. Blackout dates may apply.
No Place Like Home
There is no need to travel far when you live in such a beautiful state! As a token of appreciation for our local guests, all Maryland residents can enjoy 10% off per night.
*Rates cannot be combined with any offers. Blackout Dates may apply. Must show proof of eligibility upon check in. Click on Special Rates when booking online to claim your discount.
Military Appreciation
We deeply appreciate the brave individuals who serve and protect our nation and are happy to offer a 10% discount per night to our veterans and active-duty military guests.
*Rates cannot be combined with any offers. Blackout Dates may apply. Must show proof of eligibility upon check in. Click on Special Rates when booking online to claim your discount.
Private Boat Charter
Private Boat Charter
Embark on a memorable journey aboard our Hinckley 40′ Picnic Boat, Overcomer, departing right from our dock in a tranquil cove just off the Chesapeake Bay.
Captained Private Charters – Up to 6 passengers
- 2-hour – $1300
- Half-Day – $1900 (9am-12pm or 1pm-4pm)
- Full-Day – $3500 (9am-4pm)
Please call us at 410-745-5053 to book your private charter.
All charters are subject to Maryland State Sales Tax (6%), Amusement Tax (0.5%), and Service Fee (20%). Captain gratuity is not included. 24-hour cancellation policy required for full refund. All food & beverage must be obtained from The Oaks Waterfront Hotel. No outside food or drinks is allowed. Requires 48 hours advance notice.
Photo Credit: Michelle Whitley
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