The Oaks Waterfront

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The Oaks Waterfront ✨ Boutique Hotel & Wedding Venue Located on a cove off the Chesapeake Bay, just an hour from Annapolis and minutes from St.

Michaels, Easton and Oxford, The Oaks Waterfront offers spacious guest rooms and extraordinary waterfront event facilities. We are close enough to make your getaway spontaneous, your conference productive, your wedding a joyous gathering of family and friends. And yet, in every other sense were far enough away to become your own private corner of the world. Locally owned and managed, The Oaks Wate

rfront provides an exclusive retreat with the feeling of home. Mailing Address: PO Box 187 Royal Oak, MD 21662

Psst... our accommodations are just as exquisite midweek as they are on the weekend. Indulge in the ultimate Summer Midw...
12/06/2024

Psst... our accommodations are just as exquisite midweek as they are on the weekend. Indulge in the ultimate Summer Midweek Escape 💛 where sumptuous luxury meets waterfront tranquility, plus enjoy 20% off your final night! Simply book 2 or more nights between Sunday-Thursday and save...

Celebrate your next special occasion at our hotel to experience the best Maryland Eastern Shore getaway. Book one of our travel specials or packages today.

22/05/2024
🎶LIVE MUSIC🎶 this Wednesday! ☀️🍹🌊
20/05/2024

🎶LIVE MUSIC🎶 this Wednesday! ☀️🍹🌊

🌄 Take a well-deserved break from the hustle and bustle of daily life! Whether you’re looking for adventure or simply se...
14/05/2024

🌄 Take a well-deserved break from the hustle and bustle of daily life! Whether you’re looking for adventure or simply seeking a relaxing getaway, The Oaks has everything you need to make it happen. 🚣 We have a wide variety of summer activities in St. Michaels with plenty for everyone to do in this beautiful area of Maryland. ☀️

Searching for the best activities in St. Michaels, MD? There is a wide variety of fun summer activities with plenty for you to do in this beautiful area of Maryland.

🤩🤩🤩
13/05/2024

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🥂 A toast✨ to the ones who always have your back, Happy Mother’s Day 🤍Brooke Tyson PhotographyJ Starr's Flower BarnVinta...
12/05/2024

🥂 A toast✨ to the ones who always have your back, Happy Mother’s Day 🤍

Brooke Tyson Photography
J Starr's Flower Barn
Vintage Veils, LLC.

01/05/2024

The Pergola X is always the perfect (dependable) backdrop! 😉🧡🍑

Contact Us For Your Custom Pergola X:
📲 (410) 504-3673
📧 [email protected]

🎉 Your wedding should be as unique as your love story! 💖 Break away from tradition and make your special day stand out. ...
29/04/2024

🎉 Your wedding should be as unique as your love story! 💖 Break away from tradition and make your special day stand out. From split celebrations to yacht weddings, we've got all the inspiration you need to create a day you and your guests will never forget. 🌟

As couples increasingly seek to put their own stamp on their special day, unique weddings are taking center stage.

More shore details 🩵⚓️🦀so pretty they needed a part two✨
28/04/2024

More shore details 🩵⚓️🦀
so pretty they needed a part two✨















🌷 There's still time to savor the season. Escape to the Shore this spring for a relaxed and elegant vacation with our Sp...
23/04/2024

🌷 There's still time to savor the season. Escape to the Shore this spring for a relaxed and elegant vacation with our Spring Getaway Special. ⛵ Get 30% off your third night when you book a stay of three or more nights before May 15th!

Set on a quiet cove just off the Chesapeake Bay, our St. Michaels, MD hotel offers spacious guest rooms, luxury private cottages, event facilities and more.

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23/04/2024

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Exciting install taking place this week at the new Acorn Cottage .
The view from this tub just says
RELAX✨🥂.
Stay tuned for updates as our team works their magic.
design

Lead designers & of interiors.

22/04/2024

Cheers to the weekend!!!

20/04/2024

🌸 Save-the-date for an unforgettable afternoon of Mother’s Day fun, amazing food, views & flowers on the dock 🌊

Sunday, May 12th 12-2pm✨

🌷RSVP by calling us at 410.745.5053 x 102

✨ Boutique Hotel & Wedding Venue

All the pretty little details 🩵⚓️🦀*part one
14/04/2024

All the pretty little details 🩵⚓️🦀

*part one















09/04/2024

Thank you to Magazine for featuring our design for The Oaks Waterfront in your latest issue!

Lead designers: Carol Alfenito Wheeler and of Jamie Merida Interiors
📸 Robert Radifera Photography/ Stylish Productions

Sunday weddings have their own special feel✨Elizabeth & Ethan 06.04.23 🤍🌿Madison Berlen Photography LLCSeaberry Farm    ...
07/04/2024

Sunday weddings have their own special feel✨

Elizabeth & Ethan 06.04.23 🤍🌿
Madison Berlen Photography LLC
Seaberry Farm



Flowers on the trees & warmer days ahead 🌺☀️Brooke Tyson PhotographyJ Starr's Flower BarnVintage Veils, LLC.
05/04/2024

Flowers on the trees & warmer days ahead 🌺☀️

Brooke Tyson Photography
J Starr's Flower Barn
Vintage Veils, LLC.

02/04/2024

This was fun to design in The Oaks Waterfront Bridal Cottage: a place for the bride and her bridesmaids to get their hair and makeup done!

Lead designers: Carol Alfenito Wheeler and Leigh Draper of Jamie Merida Interiors
📸 Robert Radifera Photography/ Stylish Productions

More photos from the guest cottages: https://jamiemerida.com/blogs/portfolio/guest-cottages-at-the-oaks

From our family to yours🐰✨
31/03/2024

From our family to yours🐰✨

29/03/2024
⛵ As winter melts away, we invite you to the Eastern Shore where you can sail into spring with a rejuvenating escape! 🌼 ...
26/03/2024

⛵ As winter melts away, we invite you to the Eastern Shore where you can sail into spring with a rejuvenating escape! 🌼 Enjoy 30% off your 3rd night through May 15th and treat yourselves to some uninterrupted time sipping wine on the deck, soaking up the warm sun, and exploring the Shore...

Celebrate your next special occasion at our hotel to experience the best Maryland Eastern Shore getaway. Book one of our travel specials or packages today.

26/03/2024
23/03/2024
It’s the longer days & softer shades of Spring for us 🌿🩵
21/03/2024

It’s the longer days & softer shades of Spring for us 🌿🩵



Green & serene 💚Surrounded by the signature color of Spring, perfectly lush lawns & gardens, our meticulously manicured ...
17/03/2024

Green & serene 💚

Surrounded by the signature color of Spring, perfectly lush lawns & gardens, our meticulously manicured property is always dressed to impress 🌿✨

Chelsea Blanch Photography


Recharge in spring splendor with a retreat to St. Michaels. ⛵ Nestled along the serene banks of Maryland's Eastern Shore...
11/03/2024

Recharge in spring splendor with a retreat to St. Michaels. ⛵ Nestled along the serene banks of Maryland's Eastern Shore, St. Michaels beckons with its mild weather, stunning scenery, and a plethora of activities to refresh both body and soul. Discover why St. Michaels is the perfect destination for your spring escape. 🌷

Recharge with a getaway to enjoy spring in Maryland! Savor mild weather, stunning scenery, and a plethora of activities to refresh both body and soul.

📍Friday Night plans ✔️✨
08/03/2024

📍Friday Night plans ✔️✨

Give the gift of an indulgent experience✨🎁🥂The Oaks’ gift certificates, purchased in any amount can be redeemed for exqu...
20/12/2023

Give the gift of an indulgent experience✨🎁🥂

The Oaks’ gift certificates, purchased in any amount can be redeemed for exquisite food & beverages in The Oak Room bar and/or luxury lodging in our boutique hotel.

Guests may use their gifts to add special packages, or in-room enhancements such as cheese platters & bottles of bubbly!

Call us to purchase 410.745.5053
Certificates will be delivered digitally✨

https://the-oaks.com/gift-certificates

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