Great Oak Manor in
Chestertown (MD)

What a lovely experience my husband and I had this weekend. Our friends were renewing their vows and this was so attentive to their guests that I was really impressed. I would recommend this venue if you are looking for class and elegance!

My wife and I went here for our recent BABYMOON. It was THE BEST! Our first evening we were greeting by a team featuring Brielle and Calin, a tremendous duo capable of satisfying even your most lavish of requests. A+++ Experience. Throughout our stay... We had THE MOST DELICIOUS dinner @ the Manor, made with the freshest of ingredients, presented in the most beautiful fashion. We enjoyed two breakfasts on site, both fresh and wonderful. We loved basking by the fire pits enjoying the magnificent grounds and sunsets/sunrises, we ventured to their private beach, another remarkable site to behold. Brielle and Calin, the nicest, kindest humans, looking out and thinking of everything you might need during your stay made it the most accommodating and great experience from check in to check out. The house is exquisite, the rooms are spacious and lavish, the grounds are kept up to perfection, we had THE BEST extended vacation here. Highly recommend, WILL return!

Prior to the new owners taking over and redecorating in 2022, Great Oak was a charming country manor house filled with antiques and character. Now the interior is just another generic hotel with boring modern rooms resembling a Wayfair ad.

The Great Oak Manor offers an exquisite blend of luxury, comfort, and charm. I have stayed at The Manor several times, and the experience has always been relaxing and rejuvenating. From the moment you arrive, the warm, welcoming ambiance greets you, and the attentive staff makes you feel right at home. The food is a highly curated gastronomic experience. I've never eaten an average meal here. I highly recommend you give it a try.

This was our first visit to Great Oak Manor and we absolutely loved it! Starting with our phone call for a reservation with Corrine (who was lovely) to our arrival and weekend stay, we could not have felt more welcomed. Corrine, young Werten and Calin made us feel at home, and Mr. Werten (owner) was a pleasure to talk to. The morning breakfasts were delicious and the bar offers a wonderful way to ease into the evening. The grounds are lovely and the views of the Chesapeake Bay are terrific. We look forward to our next visit!

This is a beautiful property with a classy, elegant vibe that is perfect for fun and relaxing trips for couples or families. The building and grounds are gorgeous and there are plenty of areas to enjoy the view, including a small private beach. The staff is wonderful, Corrine and Werten are so thoughtful. They have complimentary snacks and coffee, binoculars to watch the bay, spacious rooms with beautiful views, and plenty of activities to keep you busy like a library, board games, yoga, and bikes. The breakfast is delicious. You won’t want to leave!

My recent stay at Great Oak Manor left me utterly impressed and longing for more. From the moment I arrived, I was enveloped in unparalleled hospitality that surpassed even the finest experiences I've had in major 5-star hotel chains. The attention to detail in ensuring every guest's comfort is evident in every aspect of the manor. What truly sets Great Oak Manor apart is their unwavering commitment to personalized service. They go above and beyond to anticipate and fulfill every want and need, making each guest feel truly valued and cared for. The unique personal experiences offered at the manor add an extra layer of charm, making every moment feel special. Staying at Great Oak Manor felt like stumbling upon a hidden gem. I left feeling as though I had discovered a well-kept secret and can't wait to return as a regular guest. I'll be enthusiastically recommending it to everyone in my circle. As someone who wouldn't have typically imagined myself visiting a rural location in Maryland, I was pleasantly surprised by how much I enjoyed my time there. I'm already eagerly looking forward to returning in the summer to explore more of the area, ride my bike, and bask in the beauty of the bay. In short, Great Oak Manor offers an unforgettable experience that is unmatched in hospitality, and I can't wait to return for another memorable stay.

Great Oak Manor saved my wedding weekend. The staff was accommodating, friendly and made all of our guests feel very welcome. The location is phenomenal with the ability to look out over the water. We ate breakfast both days and it was delicious. This is THE place to stay in Chestertown.

I had the pleasure of spending three days at Great Oak Manor in March 2023 for a business related retreat. I had a fabulous experience. The service was greater than excellent throughout every single second of my stay. I had at least one breakfast, lunch, and dinner at the hotel and the food provided by Chef Winston was impeccable, flavorful, and healthy! The property is peaceful - beautiful, private, and safe - and just emanates peace over everyone. I loved my hotel room but also the gathering spaces on the main floor. As a book lover, my favorite space was the library. I was happy to know that the owners thoughtfully filled the library with some books from a local bookstore. Every detail has been thought of at the hotel, including as pictured fresh cut flowers in the hallways. I hope you enjoy your stay at Great Oak Manor!

Our stay at Great Oak Manor was magical. I attended the yoga and meditation retreat with friends and the experience exceeded my expectation. The Manor is beautifully designed and situated on the Chesapeake Bay for the most gorgeous water views. My room was very nice with a fireplace and a modern bathroom with Molton Brown shampoo and Bath Wash. I can't say enough about the manager and staff - so attentive Additionally the executive chef made sure every meal was a dining experience. This is a perfect getaway and easy drive from the Philadelphia area.. I will definitely return this summer and next fall.

We had an amazing two-night stay at the Great Oak Manor that started with our warm welcome from Corinne. Just walking through the front door created the feeling of visiting a long-lost family member's house in the country. It's not a hotel, and it's not a bed & breakfast—it's an incredibly comfortable home away from home where everything is perfectly in its place and curated to inspire curiosity and induce tranquility. The common areas are recently renovated and freshened, with a bar installed for guests to gather and connect. The library's amazing collection, combined with its ample, luxurious seating, creates the perfect atmosphere to get lost for a few minutes or a few hours. Our room was beautifully appointed and had its own fireplace, which we lit one evening to enjoy cocktails and conversation. The downstairs refresh and renovation are coming to the rest of the property, which will no doubt amplify the entire experience. We got to briefly meet the owner and spend time with other members of the Manor team, Werten, and Winston. Every engagement felt personal like they've known you for years, and their focus on delivering five-star service never wavers. Well done Great Oak Manor! We'll definitely be back!

We held our wedding weekend at GOM and it was more than perfect! Holly was so responsive and helpful during the planning process - we ended up renting the entire place; All of our guests stayed at the manor for the weekend and everyone loved it! The property and views are gorgeous, the rooms are beautiful, and all of the staff were wonderful. The beds are so comfy too! Friday night we had a welcome dinner on the beach and Saturday was our wedding. We will definitely be returning for an anniversary trip!

Great Oak Manor is indeed a hidden beauty in Chestertown, MD! We were greeted at the door, our bags taken to our rooms…. Wow! What a great welcome! We were supposed to be there for two nights but stayed for a third. What a homely place to visit; it surely was like a home away from home! Coming downstairs and hearing soothing music playing or just being able to sit by the fireplace to relax makes this B&B stand out. Staff were always available, pleasant, professional and helpful. Our room was very spacious and clean and bed was very comfortable; the view from our room overlooking the water was fascinating…. seeing the sunset over the water from our room was quite a view. We did not get to visit the marina or private beach….it was just too cold; we will definitely return at a warmer time of the year!

The Great Oak Manor is wonderful place to step out of your daily life and slow things down. It was the ideal place for my wife and I to escape and reconnect. The location is perfect, quiet and serene, surrounded by water and nature. And the innkeepers couldn't have been more gracious, they made us feel like we had stayed there many times before. Our room was lovely, clean, and comfortable. We look forward to returning!

Our experience at Great Oak Manor was exceptional. While the weather was dreary, The warmth of the staff and Manor well made up for the rain. The Manor itself was beautiful! The cleanliness and attention to detail and hospitality was unsurpassed to any B&B we had ever enjoyed. Breakfast was delicious and the special touches that are around every corner, make this experience one the most special. We will be back and we expect that family and friends will make the trip…it’s well worth it! This place has the feel of going back in time…If you are an “old soul”-young or old- this place Is for you. On our next visit, we will schedule dinner 3 days in advance. If dinner is anything like breakfast, I have know doubt, it will be exceptional. Dave and Laurie Freese, Salisbury, MD

My husband and I had a wonderful one night stay at the Manor. We were greeted warmly by one of the inn managers who was friendly and helpful giving us a tour and offering to make us dinner reservations if we didn't already have them. The weather was cold and windy but inside was warm and comfortable. The Manor is beautifully decorated with such a Downton Abbey feel. Please note that it was impeccably clean! (Always important but especially during these times) We stayed in the Marmaduke room which is large, bright and comfortable with beautiful views of the bay and sunset. Breakfast in the morning was all delicious (try the homemade granola). We would love to come back again in the warmer months to take advantage of the beautiful grounds and all they have to offer, however staying in with our in room burning fireplace lit was the perfect cozy romantic night we were looking for. (Highly recommend fireplace season) Thank you for providing exceptional hospitality and a wonderful stay.

We stayed at the White House for a family wedding at the Manor and it was perfect to be so close to all the festivities and the rest of the family. The venue was beautiful for the wedding and the house was just perfect. We had so much fun with the expansive grounds and the pool table inside! The house really is huge enough for many more guests. One suggestion would be to convert one of the rooms to bunks for more kids and /or Singles. We loved our stay, and Holly and the innkeepers were so accommodating.

We are planning our wedding here for 2021 and are crazy excited! The Manor is meticulously maintained and located in such a serene setting. With Chestertown nearby and a ton of great amenities on site, this is a fantastic spot to spend a weekend. Each time of year offers benefits, from kayaking and the private beach in the warm months, to roaring fireplaces and colorful foliage in the colder ones. Holly and the team have been incredible to work with and we look forward to making lasting memories here. **Update** Our wedding was phenomenal! We hated leaving. All of our guests also had an amazing time which put us at great ease. Joe made the coordination between vendors extremely easy and he and Barb took great care of our guests. Such a relaxing atmosphere that felt exclusive yet unbelievably relaxing and low-key. We would not have changed a single thing, it was perfect! We’ll be back very soon.

My family and I enjoyed our two days at Great Oak Manor immensely. What a delightful and memorable experience we had! We deeply appreciated the gracious hospitality and beautiful house and grounds. My husband loved kayaking on the Bay. Delicious breakfast, lovely private beach with multiple hammocks and fire pits. It's a splendid, beautiful, and FUN place to relax and recharge. We look forward to returning soon!

From the time we pulled up until the time we left we received nothing but professionalism and love. It was an amazing experience. The room and bathroom were very clean. The food was amazing breakfast and dinner. The fireplace in room made the trip so much more relaxing. The staff was more then amazing and always respectful to us. I highly recommend Great Oak if you are looking for peace and quiet while at the same time being able to enjoy yourself. Definitely will be back.

We loved our experience! Joe, the Innkeeper, could not have been more accommodating. The breakfasts were out of this world! Our compliments to the chef! And the grounds and views are so inviting and relaxing. We’ve just returned home and already booked a return visit. Can’t wait to see their renovations too! Highly recommend Great Oak Manor!

My wife and I stayed 5 nights and had a small wedding celebration for 18 guests. We found Great Oak just a few months ago doing random Google searches for alternative wedding venues after our initial venue never opened because of the pandemic. Great Oak became available to us after a larger wedding on our weekend was rescheduled. Holly helped us plan our wedding in just a few weeks. The food from appetizers included stuffed mushrooms and oysters multiple ways, dinner and dessert was amazing. The service provided by Joe and staff for food delivery and bartending was top notch. We felt comfortable and at home during our entire stay. It also felt very private to us for staying at a B&B. We loved every one of our morning breakfasts which were special and different every day. The property and scenery of the bay was beautiful. It alone was enough for us to book originally. We will return to Great Oak as will many of our friends that celebrated this past weekend with us. Many thanks to the entire staff at Great Oak.

My husband and I spent a weekend at Great Oak Manor in late June. The location is beautiful, right on the Chesapeake Bay with great views and a nice breeze even during those 90+ degree summer days. We took full advantage of the kayaks and the private beach available for guests and even went swimming, which was lovely. The grounds and exterior of the manor are beautiful and well maintained. The breakfast was good, would have been nice if there was salt and pepper and other condiments available, plus more outdoor seating. Our first morning only three tables were setup. The staff was very polite and friendly. For the price of our room (Mamardukes) we did expect a bit more. The bed linens were luxurious and the room was nice but the bathroom needs a lot of updates. The bathtub was rusty and to be honest, a bit unappealing. We did not look forward to showering. There was no blow dryer in the bathroom. Other than these minor items, we had an amazing stay and would definitely come back. The Manor is only 2 hours from DC and is a great place to relax and unwind. Thanks for a great stay!

My boyfriend and I along with our dog spent a weekend at Great Oak Manor and had a fantastic stay. We stayed in the Sterling Room because it allowed dogs to stay and it was super clean. The carpet in the bedroom was incredibly soft and cushy. The B&B overall was very clean and beautiful and the grounds were immaculate. The breakfasts were fill and delicious as was the dinner which was served at an additional cost. They do offer life vests for the water equipment (kayaks, canoe, paddle boards) as well as beach towels which is awesome since we forgot to pack ours. Management was beyond friendly and helpful. I can’t wait to book another stay!

My wife and I eloped at the Great Oak Manor. We were treated very well. The room was large and well decorated. It had a decent sized TV and an assortment of books. The breakfast was unique and delicious. The ceremony was beautiful. The property is beautiful. The Manor is beautiful. Could not be happier with my experience.

A lovely Manor. Holly could not have been more welcoming. We only stayed one night. Our room was very nice though my husband was not happy I booked one on the third floor. It was very pretty with a nice large bath. The breakfast the next day was wonderful. The grounds and views are amazing. It is a beautiful place and I'm very happy we stayed there. I'd love to go back.

The manor, grounds and view of the bay were absolutely wonderful. Holly, the innkeeper was really great. She made us feel at home, gave us a great welcome and tour of the amenities when we arrived and was always pleasant and attentive. The architecture, rooms furnishings, books, paintings all made us feel very special. The peace and quiet of the water and surrounding woods was very relaxing. Breakfast was delicious and we loved making use of the kayaks and bikes. Our room was clean, large and comfortable. The only thing that needed improvement was that the water pressure in the shower was very week. Absolutely loved our stay and we will be back!