The Oaks Waterfront

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

This past week, we had the honor of hosting the first annual Witches Paddle Board event in partnership with Breastcancer...
10/18/2025

This past week, we had the honor of hosting the first annual Witches Paddle Board event in partnership with Breastcancer.org, the Clark Comprehensive Breast Center, and Sara Biden. 💕🎗️

Cancer has affected us all, and a diagnosis can feel life-altering.

But events like this remind us of the power of community and how support, understanding, and shared experiences can make a real difference.

Thank you so much to everyone for coming out and supporting this cause!

Photography:

An Evening with Elin Hildebrand was a success! 📚🥂Thank you to everyone for coming out — and a huge thank you to , .smoke...
09/24/2025

An Evening with Elin Hildebrand was a success! 📚🥂

Thank you to everyone for coming out — and a huge thank you to , .smokey.cat.lavender, , , and our guest of honor, , for helping us make this such a memorable event!

Photography:

🥂 A toast to an extra-long weekend, because you deserve it! 🍾✨
08/29/2025

🥂 A toast to an extra-long weekend, because you deserve it! 🍾✨

Tucked away in a quiet retreat on Maryland’s Eastern Shore, C + PJ’s coastal fairytale wedding was the perfect start to ...
08/20/2025

Tucked away in a quiet retreat on Maryland’s Eastern Shore, C + PJ’s coastal fairytale wedding was the perfect start to their happily ever after.🪻✨

Photography:
Planning:
Florals:
Rentals: .dmv
Hair and Makeup:

💍 Voted Best Wedding Venue in Maryland! ✨We’re incredibly excited and honored to share that The Oaks has been named as t...
07/17/2025

💍 Voted Best Wedding Venue in Maryland! ✨

We’re incredibly excited and honored to share that The Oaks has been named as the Best Wedding Venue in Maryland by in their Best of the City 2025 Awards publication!

As a family-run business, we’re so grateful for your continued support.

Since 2022, we’ve poured our hearts into restoring and reimagining this historic building that is a special place for so many. To receive this dream recognition just three years later is truly amazing. 🩵

Thank you for being part of our story…we can’t wait for what’s next! 🍾🥂

Shelby and Cole’s dockside vows were the perfect start to their Eastern Shore wedding celebration. 🩵✨After the ceremony,...
06/04/2025

Shelby and Cole’s dockside vows were the perfect start to their Eastern Shore wedding celebration. 🩵✨

After the ceremony, the dock transformed into a space for cocktails before guests gathered in the ballroom for the reception. 🍾🥂

Cheers to Shelby & Cole—we loved being part of your day!

Photos:
Planning:
Flowers:

Golden hour on the water. 🌅✨Unwind with an Aperitivo Cruise aboard our new Hinckley yacht — complete with drinks and the...
05/19/2025

Golden hour on the water. 🌅✨

Unwind with an Aperitivo Cruise aboard our new Hinckley yacht — complete with drinks and the best views of the Chesapeake Bay at sunset. 🥂

Spots are limited so call our guest services team to book this experience.

📲 410-745-5053

*Open to hotel guests and the general public!

Unwind on the water and experience the ultimate golden hour with our weekly Evening Aperitivo Cruises, starting this wee...
05/12/2025

Unwind on the water and experience the ultimate golden hour with our weekly Evening Aperitivo Cruises, starting this week! 🌅✨

Step aboard Overcomer, our stunning new Hinckley yacht, for a golden hour escape inspired by the Italian tradition of aperitivo—a time to unwind, connect, and sip something refreshing as the sun sets over the water. 🥂

Cruises run every Tuesday and Thursday at 4pm and 7pm (weather permitting), with space for up to 6 guests.

Call our guest services team for more information!

Warmer days are just around the corner, and we’ve got everything you need for the perfect spring escape. 🌷🪺Plus, don’t f...
04/09/2025

Warmer days are just around the corner, and we’ve got everything you need for the perfect spring escape. 🌷🪺

Plus, don’t forget to take advantage of our spring specials before it’s too late.

Visit our website for more details.

A fresh season calls for a fresh start. 🧘‍♀️🌷☀️Wake up feeling renewed and rejuvenated, knowing you scored the best deal...
03/25/2025

A fresh season calls for a fresh start. 🧘‍♀️🌷☀️

Wake up feeling renewed and rejuvenated, knowing you scored the best deal on your spring getaway.

🌿The Suite Life - Book a minimum of 2 nights in any of our suites and get 25% off the last night of your stay.

🌿Spontaneous Spring Getaway - Enjoy 15% off the last night of your stay when you book the same week of your arrival.

🌿Stay a Little Longer - Book 3 or more nights and enjoy 20% off the last night of your stay.

*For new reservations only. Cannot be combined with other offers. Blackout dates may apply.

Address

Easton, MD

Telephone

+14107455053

Website

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