Great Oak Manor

Great Oak Manor Great Oak Manor provides exceptional hospitality, and an extraordinary setting on Chesapeake Bay. We are a smoking-free. Pets are prohibited.

It is our vision that guests of Great Oak Manor enjoy gracious hospitality, a memorable experience, and this extraordinary setting--while focusing on the things that are important to them. Please note that Great Oak Manor is an adult property, welcoming guests 12 years of age and older.

This May, Taste of Great Oak Manor welcomes Chef of Anju in Washington, DC for "A Journey Through Korea" — an immersiv...
03/26/2026

This May, Taste of Great Oak Manor welcomes Chef of Anju in Washington, DC for "A Journey Through Korea" — an immersive culinary experience shaped by bold flavor, cultural storytelling, and unforgettable moments at the table.

A four-time James Beard Foundation Award semifinalist, Food & Wine’s 2021 Best New Chef, and the RAMMY 2024 Chef of the Year, Chef Barreto is known for his vibrant, modern approach to Korean cuisine — where fermentation, spice, and balance come together in ways that feel both deeply rooted and completely fresh.

Over the course of the weekend, you’ll experience: ✨ Multi-course collaborative meals
✨ Live cooking demonstrations
✨ Tastings that explore layers of Korean flavor
✨ Fireside conversations with the chef
✨ And the kind of connection that only happens when great food meets the right setting

Set along the Chesapeake Bay, this is your chance to slow down, savor something new, and turn a weekend into a true getaway.

📍 May 15–17, 2026
💫 $500 per person (event activity fee; rooms sold separately)

Come for the food. Stay for the experience. Leave with a story!

🔗 Book your stay now at greatoakmanor.com!

We’re thrilled to welcome an incredible lineup of chefs to our 2026 series! Each exclusive weekend features a guest ch...
02/27/2026

We’re thrilled to welcome an incredible lineup of chefs to our 2026 series!
Each exclusive weekend features a guest chef experience complete with live cooking demonstrations, hands-on kitchen moments, and thoughtfully curated seasonal menus—all set against our beautiful Eastern Shore waterfront.

Follow along as we spotlight each chef and their upcoming weekend. Rooms fill quickly, so be sure to reserve your stay and make it a true culinary getaway.

View the full calendar + book your experience: https://greatoakmanor.com/tasteof/

Featured chefs include

Slip away from the noise and return to calm and connection. Love on the Bay is an intimate couples weekend designed for...
01/13/2026

Slip away from the noise and return to calm and connection.

Love on the Bay is an intimate couples weekend designed for presence, ease, and romance—where the Bay sets the rhythm and everything else slows down.

Enjoy chef-prepared meals, unwind with an in-room massage, savor quiet mornings and candlelit evenings, or even move together during an evening of salsa.

This weekend isn’t about a packed itinerary. It’s about the two of you.

February 13-15, 2026 at Great Oak Manor.

Reserve your Love on the Bay escape at greatoakmanor.com!

RomanticGetaway

This summer, hit pause - and reclaim your calm.Join us next month for the StressLess Retreat at Great Oak Manor (July 11...
06/17/2025

This summer, hit pause - and reclaim your calm.

Join us next month for the StressLess Retreat at Great Oak Manor (July 11–13), a peaceful, powerful weekend designed for women who are ready to breathe deeper, move slower, and reset by the water.

🌿 Gentle movement & mindfulness
🌿 Practical tools for stress relief
🌿 Your personalized resilience plan
🌿 Bayfront serenity, sisterhood, and soul care

Led by two extraordinary women:

Dr. Denee Choice – Double board-certified physician, and executive coach, here to help you understand stress, reclaim your energy, and design a path forward.

Luisana Tejada .tejada – Certified Vinyasa yoga instructor whose practice is rooted in self-love, stillness, and transformation through movement and breath.

Together, they’ll help you build lasting tools for resilience—in a tranquil bayfront setting designed for your healing.

Space is extremely limited to preserve the intimacy of this retreat experience, and just a few reservations remain! Visit our website for more details or call us to book today.

Don’t miss it—tonight’s the night!We opened our doors to the Savor The City cameras, and what happened behind the scenes...
05/29/2025

Don’t miss it—tonight’s the night!
We opened our doors to the Savor The City cameras, and what happened behind the scenes was just as special as what made it to air.

Take a peek at these behind-the-scenes moments—kitchen prep, porch conversations, and all the heartfelt hospitality that makes Great Oak Manor shine.

Big thanks to the incredible production team and our amazing community for cheering us on. Tune in tonight!

TV One’s Savor The City
🗓 Thursday, May 29
⏰ 8:00 PM ET
📍 Only on TV One


The Bay is calling you back.Come and take a break at Great Oak Manor—where stillness lives, connection deepens, and each...
04/25/2025

The Bay is calling you back.

Come and take a break at Great Oak Manor—where stillness lives, connection deepens, and each sunrise is a fresh start. Come back to the manor. Come back to yourself. Now booking through May 2026.    

 

Great Oak Manor on a snowy day
01/16/2024

Great Oak Manor on a snowy day

Snowy Firepit / Chesapeake Bay
01/16/2024

Snowy Firepit / Chesapeake Bay

From the first bite to the last, enjoy exquisite flavors here at Great Oak Manor.✨
01/15/2024

From the first bite to the last, enjoy exquisite flavors here at Great Oak Manor.✨

Cozy season is upon us. There's nothing like a good book and a nice cocktail to wind down your day. 🥃📖
01/13/2024

Cozy season is upon us. There's nothing like a good book and a nice cocktail to wind down your day. 🥃📖

Indulge in the art of flavor at Great Oak Manor, where we serve delicious breakfast, lunch, and dinner for all lodging g...
01/09/2024

Indulge in the art of flavor at Great Oak Manor, where we serve delicious breakfast, lunch, and dinner for all lodging guests.

Address

10568 Cliff Road
Chestertown, MD
21620

Telephone

+14107785943

Website

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