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Venues in Chestertown, MD,
(410) 778-5943

About Us

Great Oak Manor is a destination wedding venue based in Chestertown, Maryland. Talk about a welcoming venue for you and your guests! With incredible and scenic views of Chesapeake Bay and a private, intimate beach, this venue provides a fun, exciting and warm atmosphere for all weddings. They love to host weddings in a classy Eastern Shore style!

Facilities and Capacity
Their waterfront glass conservatory can host dinners, rehearsals and that exciting farewell. This venue can host up to 200 guests. With their 12 acres of lush and sprawling green landscapes, this venue has all of the gorgeous backdrops for stunning photos.

Services Offered
Great Oak Manor offers exceptional service to help their clients. They desire for all of their couples and guests to have a memorable and comfortable stay. Their services include:

  • Accommodations
  • Bridal suite
  • Pet friendly
  • Ceremony
  • Elopements
  • Reception area for tents

Juliana DeAngelis

2 out of 5
Quality of Service:
  • Responsiveness:
  • Professionalism:
  • Value for Cost:
  • Flexibility:
  • In early July 2020 my fiance and I drove out to the Eastern Shore to tour wedding venues. We saw several but fell in love with Great Oak Manor ("GOM"). The manor and grounds are absolutely beautiful! Also, GOM allows pets and we have two pups that absolutely have to be a part of our special day. I was soooo relieved to have found our venue and we provided GOM with a $500 deposit to reserve our date. Holly, the innkeeper, emailed us the contract about a week or two later. The contract didn't have a force majeure clause (a clause that excuses performance of the contract for both parties if there is a pandemic/act of god/fire, etc.) or a rescheduling provision - so we asked Holly for GOM to supplement the contract with language they had used in the past. She requested that we draft language that we thought was "reasonable," so we did (we are both attorneys). We submitted the draft language to her within a week and waited OVER A MONTH for GOM's attorney to review the language and su... Read more

    responded with the following comments.

    We are so sorry we weren't able to reach an agreement and we wish you the very best as you are planning the details for your special day. We understand what a challenging and emotional time this is to be planning a wedding and have adjusted our contracts to provide flexibility for wedding couples while also protecting our business to ensure we are able to host brides for many years to come.

    Frequently Asked Questions about Venue

    Do you have a site fee for wedding receptions at your venue?


    What is the starting site fee for wedding receptions during peak season?

    $ 7,581.00

    What is the starting site fee for wedding receptions during off-peak season?

    $ 3,531.00

    Do you have a site fee for wedding ceremonies at your venue?


    What is the starting site fee for wedding ceremonies during peak season?

    $ 7,571.00

    What is the starting site fee for wedding ceremonies during off-peak season?

    $ 3,493.00

    Which of the following are included in starting site fee?


    How many event spaces or rooms does your venue offer?


    Describe your venue

    Beach, Inn/B&B, Mansion, Waterfront

    What kind of settings are available?

    Indoor, Uncovered Outdoor, Scenic Views

    Which of the following wedding events does your venue service?

    Ceremony, Reception, Bridal Shower, Elopements, Rehearsal Dinner

    What event services do you offer?

    Accommodations, Outside Vendors, Pet Friendly, Wifi

    What transportation and access is available?


    What months are included in your peak season?

    May, June, September, October

    What months are included in your off-peak season?

    January, February, March, November, December

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