Great Oak Manor

10568 Cliff Rd , Chestertown, MD 21620-4115 USA (Show map) Diamond Collection

Professionally Inspected & Certified Diamond Collection


One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay just outside of Chestertown in Maryland's Eastern Shore. With large common rooms, beautifully appointed guest rooms, and comfortable outside seating areas shaded by majestic Oak and Walnut trees, the Manor affords its guests ample and comfortable areas in which to relax.The Manor will meet your every need with 1,200 ft. of waterfront, a private beach and the most beautiful sunsets on the Eastern Shore. Enjoy our canoe, kayaks and SUPs out on the Bay. Visit the countryside on one of our bicycles. Or just relax with a good book in one of our hammocks or Adirondack chairs by the water. In cooler weather, relax with a glass of wine or cup of tea by the fireplace in our large library. There is something to do for everyone.



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  • Guest room4.5
  • Service4.7
  • Value4.3
  • Cleanliness4.6
  • Onsite Dining4.5

A wonderful experience!

5 on September 14, 2018

This beautiful B&B is probably one of my favorites. The setting is peaceful, quiet, and memorable. The view of the Chesapeake Bay from the property is fabulous. Our room was cozy, breakfast was absolutely delicious, and the staff is very efficient. Holly and Meranda offered exceptional hospitality. We can't wait to come back and visit Great Oak Manor. No wonder this B&B meets the high expectations of Select Registry standards.

Beautiful setting

4.8 on August 15, 2017

Extremely warm and friendly staff. Beautiful setting and relaxing place to stay. They have kayaks, paddleboards and bikes available for your use. Hammocks and adirondack chairs to lounge on with a beautiful view of the bay. There is also a pool next door at the marina which is available for your use. Wonderful breakfast. Snacks made available during the day. A refrigerator made available for guest use. Extremely comfortable bed and ultra soft bed linens. The new owner have updated the place and there is a wonderful conservatory area which is great for lounging in. There was a notice that stated during Nov 1 thru Apr 1 they will give you a fire log for your in bedroom fireplace. You can also bring your pet. The innkeepers kept asking if there was anything else they could do to make our stay more enjoyable. I rated it a four on value because I thought it was a little pricey, but I only have hotel stays to compare it to. It was my first experience at a bed and breakfast and it will be hard to beat.

We couldn't imagine a better place to get married!

4.8 on September 28, 2016

Our wedding in September 2016 was absolutely incredible and Great Oak Manor was the star of the show (besides us of course). Spending the weekend and having a place where our family and closest friends could stay with us was invaluable. The house is spectacular and fits perfectly with the beautiful grounds. It was fun deciding which of our relatives and friends would stay in each of Great Oak's large and welcoming rooms. Our ceremony was by the water, complete with bay views and a nice sunset. The back yard was a great setting for our cocktail hour and the side yard was prefect for our seated dinner and dancing. The staff couldn't have been more helpful all throughout the process, and especially during the weekend. A huge thanks to Great Oak and the team for a truly unforgettable wedding for us and all our guests!!

Innkeeper Response
Thank for your kind words! Great Oak is a great spot to get married with the only Chesapeake Bay water views in Kent County. The Eastern Shore offers many things for couples or groups to enjoy! We hope you will spend your anniversary's with us in the future.. Thanks Mike

- Mike (innkeeper)

A Great Getaway

5 on June 18, 2016

Outstanding in all categories. The breakfasts are a delight, and full of surprises. It is remote enough to be out of the beaten path, but close enough to Chestertown and Rock Hall to enjoy equally outstanding dinners. There is a friendly and helpful staff if you should need anything. The rooms are of equally high standards. It would be difficult to find a better setting, with grounds on the Chesapeake Bay for relaxing and watching the sunsets over the bay. Highly recommended. Gene Larson

Innkeeper Response
Thanks for the kinds words please some see us again soon.

- Michael (innkeeper)

Beautiful B&B

5 on November 19, 2015

Beautiful property, great service, fantastic views of the Chesapeake Bay. We are already planning our next visit. H. Sheneman

Innkeeper Response
Thank you so much for your kind words, we are so thrilled that you enjoyed your stay and look forward to having you back again soon!

- Kaylin Benfield, Innkeeper (innkeeper)

Wonderful experience, our first stay in a B&B.

3.8 on October 08, 2015

The staff and Innkeepers were lovely and very helpful. Everything was just as stated on the website.

Innkeeper Response
It is so wonderful to know that you had a great experience especially as it was your very first B&B stay. We do hope that you will come back to visit us for your second B&B stay as well!

- Kaylin Benfield, Innkeeper (innkeeper)

Great stay

5 on August 24, 2015

Been to the manor twice and was best ambiance and environment I have ever experienced! Recommend you stay there it will set the standard you should expect from any provider in the industry!

Innkeeper Response
We are so pleased to know that you have enjoyed both of your stays. It is so gratifying to know that you enjoyed your experience and we do hope that you will visit us again soon!

- Kaylin Benfield, Innkeeper (innkeeper)

A Wonderful Experience!!!

4.6 on August 12, 2015

Everything was great! The staff was very courteous and helpful. All food preparations were unique, well prepared and presented. Love the old charm and country feel. Wonderful weekend getaway, looking forward to our next stay during the week.

Innkeeper Response
Thank you for your kind words, we are so glad to know that you enjoyed the staff, food and our wonderful Manor. We look forward to having you back again soon!

- Kaylin Benfield, Innkeeper (innkeeper)

Wow, what a find !

5 on August 05, 2015

What an incredibly restful place, and so close to Washington, D.C. We stayed in the Roese Room, and the pet-friendly policy allowed us to bring Lucy. The staff were great. We are telling all our friends about The Great Oak !

Innkeeper Response
It is so great to know that you enjoyed your stay. We loved meeting Lucy as well as yourselves. We hope to see some of your friends and do hope that you will visit us again as well!

- Kaylin Benfield (innkeeper)

Artist's Dream

5 on June 16, 2015

My favorite place in the world to paint and watch birds. Amazing staff, best breakfast I've ever had at a B&B worldwide. Best view. Can't say enough nice things about the character of the building, furniture, library and did I mention VIEW! Eagles, kingfishers, herons, warblers, turkeys, etc. Binoculars provided! Can't say enough nice things about the Inn, Innkeeper, staff, rooms. Favorite place on earth to paint.

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Rooms & Rates


Beautiful second floor, waterview room with sweeping views of the Bay. Fireplace and bed that looks right out to the water, our most popular room. Rise to breathtaking views of the Chesapeake Bay from a king-size bed that begs you to stay under the covers for a moment longer. Bright and airy, the Marmaduke features rich floral hues and is perfect for just gazing out at the view. With a cozy fireplace, walk-in closet and sumptuous bath, this luxury guest room is as lovely as the first land owner for which it is named. Being on the corner of the house affords the room ample space and natural lighting, also making this room perfect to act as our bridal/honeymoon suite for couples hosting their wedding at Great Oak Manor, or sharing a romantic getaway together. The Marmaduke has its own heating/cooling.

  • Maximum Capacity: 2
  • Beds 1 King


Deluxe, waterview room that boasts a handsome interior and fireplace. Situated in the middle on the second floor, the D'Oench has some of the best views.

  • Maximum Capacity: 2
  • Beds 1 King

Roese Suite

Elegant suite overlooking the estate and courtyard with a king size bed, extra sitting room with electric fireplace and spacious bathroom with skylight.

  • Maximum Capacity: 3
  • Beds 1 King

Russell Suite

The largest suite that runs the width of the mansion on the third floor and maintains echoes of the sportsmen lodge of Great Oak Manor's history.

  • Maximum Capacity: 4
  • Beds 1 King

Caulk Suite

Waterfront and spacious, the Caulk Suite is situated on the second floor and also boasts a small private sitting balcony. Garden interior theme with spectacular views of the Bay.

  • Maximum Capacity: 4
  • Beds 1 King


Quaint waterview room located on the second floor with a standing-only balcony that overlooks the grounds and Bay.

  • Maximum Capacity: 2
  • Beds 1 King

Geddes Piper

Intimate and unique, the Geddes Piper boasts an interior balcony that provides stunning views and comfortable chairs to relax in with a cup of coffee or glass of wine. This room is located on the third floor.

  • Maximum Capacity: 2
  • Beds 1 King


Lovely estate view room on the second floor with a working fireplace and accents from straight from the sea.

  • Maximum Capacity: 2
  • Beds 1 King


Lovely second floor room with a fireplace and queen size four poster bed that has several different views of the estate.

  • Maximum Capacity: 2
  • Beds 1 King

Sterling Suite

Lovely first floor suite, handicap accessible, with French door that lead out into a lovely seasonal flower garden. The suite features a separate sitting room with a pull-out sofa bed.

  • Maximum Capacity: 4
  • Beds 1 King


Tucked away on the third floor, the Ringgold offers a sweeping view of the estate.

  • Maximum Capacity: 2
  • Beds 1 King


Hyson is a third floor room with high ceilings and a standing view of the Bay.

  • Maximum Capacity: 2
  • Beds 1 King

The Carriage House

The Carriage House at Great Oak Manor is our newest accommodation. It boasts majestic views of the Eastern Shore with room for up to 6 people.It has a full service kitchen equipped for all of your cooking needs. The master is the King bedroom. The Loft area also features a Queen and a twin Fold out for extra guests.

  • Maximum Capacity: 6
  • Bathroom Private Bath
  • Beds 1 King , 1 Queen , 1 Twin

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Location Type

Marina, Chesapeake Bay waterfront, Countryside, Oceanfront, Small town


Baltimore, MD (BWI-Baltimore Washington) 80 miles

Directions to property:

10568 Cliff Rd. Chestertown, MD. 21620 Visit Web Site for printable directions from the North and the South.

Area Attractions

Antique Shopping, Art Galleries, Beach, Concert venue, Eco-tourism, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Museum, National/State parks, Nature area, Sunset Cruises, Nature Trails, Sporting Clays, Historic Washington College, Historic Churches, Chesapeake Bay, Wildlife Refuge, Maryland Scenic Highway Rt. 213, Bird Migration, Outlet Stores, Performing Theater, Picnic area, Religious Services, River, Tours, Vineyard, Winery

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Inn Details

Establishment type

Other, Historic Inn

On-site amenities

Amenities Basket, Bike rental, Coffee/Tea facilities, Conference Rooms, Copier, Electric vehicle charging, Fridge, Library, Microwave, Outdoor grilling, Parking, Piano, Private entrance, Telephone, VCR, Wedding Facilities, Wet bar, Wired internet , Golf, Tennis, Conceirge Services, Bicycles, Room safes

Room amenities

Air conditioning, Alarm clock, Bath robes, Board games, Ceiling fans, Desk, Fireplace, Hairdryer, Ironing Board, Radio, Satellite/Cable TV, TV, Wi-Fi

On-site activities

Bicycle riding trails, Bicycles, Bird watching, Canoeing, Fishing, Golfing, Horseshoes, Kayaking, Sailing, Sight-seeing, Swimming, Water sports

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  • Check In:: 11:00 - 11:00
  • Check Out:: 11:00
  • Open All Year Round: Yes
  • Smoking Allowed: Outside only Terrace outside, anywhere on the grounds
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Limited Children under 12 are welcome for family events, weddings
  • Childcare Provided: No
  • Guest Pets Allowed: Prior approval required Three pet friendly rooms
  • Disabled Access Limited

Terms and Conditions

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Richard and Holly McKee

Languages spoken


Resident Pets


About the innkeepers

Richard and Holly McKee come from Tryon, NC where they have lived for the past 13 years serving on several boards including Tryon Concert Association and Tryon Arts and Crafts School. After a career in teaching for Richard and dental sales for Holly, they trained to be interim innkeepers. So when the opportunity came to manage Great Oak Manor on a full-time basis, they couldn’t let it pass. Holly loves cooking, gardening and entertaining. Richard enjoys art, woodworking, and boating.

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  • Time Served: 9-10 AM
  • Serving Location: waterside terrace, Dining Room

Special meal options

Low fat , Restrictive , Vegetarian Inquire upon booking

Signature Dish

Farm to Table Modern
We strive to embrace using the freshest ingredients possible at Great Oak Manor. Our Innkeepers are hoping to continually expand the menu options for our breakfast tables to include ingredients from our own little garden and from local farms.They're also looking at creating a more modern approach to dishes.


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