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Venues in Chestertown, MD,
(410) 778-5943
Overall Rating
4.7 out of 5
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  • 19 Reviews


    Juliana DeAngelis

    reviews
    2 out of 5
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  • 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.

    Katherine

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    5 out of 5
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  • My new husband and I first fell in love with this picturesque, hidden gem when we toured as a potential wedding venue in Oct. 2019. We were not only memorized by the beauty of the property and the sense of calmness and serenity we felt while visiting, but we were so at ease and impressed with the hospitality when speaking with the main Inn Keeper, Holly about the possibility of hosting our 2020 nuptials there. We had been to several nice waterfront properties up and down the Eastern Shore before we went to Great Oak, but none held a candle to GOM and all it had to offer. Driving into the gates and up the gravel drive, we knew we'd eventually marry at the the Manor, and so we signed a contract that day and never looked back. Fast forward 1 year and few wedding bands later, we know without a shadow of a doubt that Great Oak was the perfect home away from home to host our closest friends and family for what has now become the best day of our lives to date. Every time we have stayed a... Read more

    responded with the following comments.

    Thank you so very much for your kind words, Katy. I appreciate your taking the time to write such a lengthy review of your wedding experience. You were such a joy to work with that you made my job so much easier. We do look forward to having you, your family and your friends visit again in the future.

    Stacey

    reviews
    5 out of 5
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  • Holly and Joe are incredible. Planned for the better part of a year, through COVID and was given so much support and treated like family when the time came. Holly is awesome.

    Brittany

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    5 out of 5
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  • This is a prefect venue for any kind of wedding. The scenery is beautiful. It is a wonderful venue.

    Jenn

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    5 out of 5
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  • Great Oak Manor can provide you a wedding experience as small or as big as you want it to be in a flexible, affordable atmosphere. We visited Great Oak Manor and immediately fell in love with the venue. A private getaway right next to the water with an incredible view - not to mention a small beach, firepits, kayaks, and hammocks. Quiet, peaceful, and overall a great place to just unplug from the daily worries. The inside of Great Oak Manor was as beautiful as the outside which aleviated the worry of rain ruining the day. The packages at Great Oak were very affordable and realistic compared to other venues that we searched. We ended up choosing the Small Wedding Package with up to 25 people and chose a catered reception dinner. Holly was a phenomenal chef and catered our wedding reception dinner. Her and her staff took care of the wedding cake or in our case a cheesecake. We were able to add on to the floral package so all of the bridesmaids and groomsmen had floral arrangements.... Read more

    responded with the following comments.

    Jenn, thank you so much for this detailed review. So helpful to others. I appreciate your kind words and your assessment of the food and service of Great Oak Manor. We look forward to seeing you and Mitch very soon.

    Paige Reffe

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    5 out of 5
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  • Great oak has been a pleasure to work with and we are very much looking forward to a magical experience. We cannot recommend them highly enough

    responded with the following comments.

    Why thank you Paige. And we haven't even made it to the good part yet. It has been a pleasure working with you both as well.

    Melissa Bishop

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    5 out of 5
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  • We are planning our wedding at Great Oak Manor for this March and Holly has been fabulous, super accommodating and helpful! We are doing a small, family wedding and the venue is beautiful, well maintained and spacious while still being very affordable.

    Morgan

    reviews
    5 out of 5
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  • We celebrated our wedding weekend with Great Oak on the weekend of November 3rd, 2018 and it was absolutely amazing! When we started looking at wedding venues I knew I wanted somewhere with an incredible view of the bay and somewhere where we could stay all weekend with our friends and family which Great Oak checked off these boxes for us! Great Oak was our first venue tour and after touring a few other similar venues we just knew Great Oak was the perfect fit for us! Holly and Richard really sold us on the beautiful property not to mention Holly was just so nice and assured us that we would have the most beautiful wedding there! We booked them a year in advance since they book up fast and throughout the year of planning if we ever wanted to stop by or had any questions Holly was always there for us every step of the way! During our wedding weekend Holly and Richard made it the beat weekend of our lives! They made sure everything went smoothly and that if we needed anything at all they... Read more

    responded with the following comments.

    Thank you Davey and Morgan. You both were a dream to work with. No problems there. We look forward to seeing you around in the future and you are always welcome at the Manor anytime. Hugs, Holly

    Kara

    reviews
    5 out of 5
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  • We just had our wedding and Great Oak and couldn't have asked for a better experience! The staff at Great Oak, Holly and Cass in particular, were amazing to work with from the beginning throughout the entire planning process. Chestertown is small and all of the vendors know each other. Great Oak has a great reputation and everyone jumped at the chance to work with Holly when I mentioned where our wedding was! I always got quick responses to my emails, someone always answered the phone when I called, and there was never a question the team couldn't answer for me. It made me feel reassured and comfortable that my venue was reliable and had true professionals working there. The venue itself is lovely. We rented out the entire house so it was filled with all of our family and friends. For the bride and groom - we stayed in the Carriage House which was an experience in itself. There was lots of hanging out on the outdoor patios, walks on the beach, and kayaks on the bay. It really is... Read more

    responded with the following comments.

    Thank you Kara and Kyle. We loved having you and your family and friends here. We wish you a wonderful life full of happiness and good health..

    Maryn

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    5 out of 5
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  • Great Oak Manor is a dream wedding venue. The manor is timeless and beautiful (carriage house is awesome!), views and sunsets incredible, and staff especially Lynne was amazing. There are more picture spots here than you could possibly do. It was great to have the manor for the whole weekend which allowed us to set up everything before hand and made it a whole wedding weekend event. We had some bumps in the road communicating at first, but everything was sorted out. The new innkeepers seem to really know what they're doing. You have to see this place to believe it!

    responded with the following comments.

    Maryn, thank you very much for your great review. It was our pleasure hosting your special day. Holly

    Jess

    reviews
    5 out of 5
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  • I would highly recommend Great Oak to any couple as the site for their wedding. We chose Great Oak Manor because it was the most unique venue we visited. The grounds are beautiful and the architecture is exquisite, which is great for guests and also for photos. We were married here in mid September 2017, and it was picture perfect. We had a very positive experience working with Holly, Jenn and their staff leading up to our wedding day and they helped to make the entire weekend easy. On our walkthrough we scoped out both the outdoor ceremony, reception areas and a back up indoor plan for inclement weather. I was impressed at how many people the venue could hold and loved that the grounds were sprawled out so guest have plenty of space. There’s a small beach, gazebo, bayside overlook, a wooded area, and separate private area with flat ground where we could have an outdoor reception and set up a massive sail cloth tent that we rented from Eastern Shore Tents and Events. What’s nice... Read more

    responded with the following comments.

    Thank you Jess for this wonderful review of your experience with Great Oak Manor. We wish all the best to you and Erik.

    Sara

    reviews
    5 out of 5
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  • We fell in love with Great Oak Manor at first sight and it only got better from there! Every staff member was so caring, thoughtful, helpful, and wanted to make our wedding as special as possible. They treated us like family and our family could have not been more impressed. They were the most incredible hosts for our wedding weekend!

    responded with the following comments.

    Thank you Sara. It was our greatest pleasure to be chosen by you for your wedding and reception. We appreciate your kind words.

    User6798854

    reviews
    5 out of 5
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  • This is the perfect venue for your dream wedding, whatever that may look like. We held an elegant ceremony on the bluff over looking the Chesapeake Bay followed by dinner and dancing under an expansive tent on the lawn. The following day was a celebration with additional family and friends with something for everyone. Lawn games, swimming, kayaking, paddleboard, hammocks, etc. A perfect location for a beautiful experience

    responded with the following comments.

    Belatedly, thank you for your great review of using Great Oak Manor as your wedding venue. We are thrilled you had such a wonderful experience. Holly-Manager/Innkeeper

    Kathryn

    reviews
    4.7 out of 5
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  • Loved everything about Great Oak! My guests were SO impressed by how beautiful the views were and the building/venue. I had so many compliments on how memorable my wedding will be due to the awesome location. The other cool aspect was having everyone stay together over the two days, we got really great quality time with friends and family. Just be sure your guests are aware of how far out it is and provide directions ahead of time. We had some snags in the schedule due to people getting lost on their way out.

    Sara

    reviews
    2.1 out of 5
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  • When I went to review this venue I was shocked when I saw 5 star reviews- but then I noticed a lot of the reviews mention "Scott & Kaylin" as the inn keepers- they were fired. I too met them when I first toured Great Oak and fell in love with the manor but months before my wedding I was called by the new management and was informed Scott and Kaylin were let go. This is where the mess began. I met with the new manager Mike who told me right off the bat that he "hates" weddings- what a thing to say to a bride & paying customer. He dissed Scott and Kaylin and basically acted like the contract they had given me was complete crap. He was very hard to establish a rapport with. Would take forever to answer emails and questions and really just put off the vibe that he could pretty much care less about our wedding. I was so stressed out leading up to our wedding and was getting zero help from Great Oak. As our wedding approached I would email to ask small questions about this and that and for ... Read more

    responded with the following comments.

    As the new Manager/Innkeeper of Great Oak Manor this past year, I am offering my apology for your very bad experience. All I can say is that none of that should have ever happened to you. The owners are horrified and want you to know that the manager at the time had medical issues and was not himself. Nevertheless, that is not a excuse but the reason .Please call me at 410-778-5943 as we wish to offer you a special deal. Best regards, Holly McKee, Manager/Innkeeper

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