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.



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

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!

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!

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!

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!

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!

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.

Beautiful, scenic, interesting!!

4.6 on May 30, 2015

A wonderful stay at Great Oak Manor! Beautiful guest rooms, with new comfortable bedding. Lovely new wallpapers and paints. Helpful staff. Tasty breakfasts. Gorgeous sunsets. Great water views. Spacious grounds, terrific for strolling along the shore. Close to historically, architecturally interesting Chestertown. Charming!! Barbara Thompson

Best Bed and Breakfast

5 on April 08, 2015

I just returned from a wonderful two stay at the Great Oak Manor Bed and Breakfast. It was so relaxing! The view and sunset was spectacular! The new owners have up dated in and around the Manor. The one improvement was new bedding and linens.The Innkeeper was very friendly and happy to satisfy your every request. She served a fabulous breakfast and dinner. You feel like a special guest. Eileen Kuhn

Quiet Retreat

4.8 on December 26, 2014

We had a great 2 night stay prior to Christmas. The house was decorated very well and property is just breathtaking being located on a former large estate. The host was outstanding and was extremely attentive and informative. She made sure all amenities were at our disposal and helped set the mood for a very relaxed experience. Being fairly secluded outside of historic Chestertown , you really got the sense of stepping back in time to a simpler period . Would highly recommend the in-room couples massage experience.

BIRDING HOT SPOT!!! spectacular view - quite relaxing

5 on May 15, 2013

Incredible view - fantastic manor - wonderful innkeeper! Incredible breakfasts! MY FAVORITE INN IN THE WORLD!!!! Time stopped for us. Bring a great book or catch up on your magazines as there are many chairs and some hammocks that say "sit, stay & enjoy!!!"

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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


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

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

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

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


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

  • Maximum Capacity: 2

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


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

  • Maximum Capacity: 2


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

  • Maximum Capacity: 2

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


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

  • Maximum Capacity: 2


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

  • Maximum Capacity: 2

Day Pass

Spend a day at Great Oak Manor without spending the night! For $80 per couple, you'll be able to use all our ammenities like kayaks, canoe, paddle boards, and you get a picnic lunch and sunset beverage.

  • Maximum Capacity: 30

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Location Type

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


Baltimore, MD (BWI-Baltimore Washington) 65 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, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, 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

Inn Details

Establishment type

Other, Historic Inn

On-site amenities

Coffee/Tea facilities, Computer, Conference Rooms, Copier, Fridge, Library, Microwave, Piano, Private entrance, Satellite/Cable TV, Videos, Washer/dryer, Wedding Facilities, Wet bar , Golf, Tennis, Conceirge Services, Bicycles, Room safes

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, Board games, CD player, Ceiling fans, DVD Player, Desk, Fireplace, Hairdryer, Ironing Board, Radio, TV, Telephone, VCR, Wi-Fi, Wired internet

On-site activities

Bicycle riding trails, Bicycles, Bird watching, Boating, Canoeing, Fishing, Golfing, Hiking trails, Horseback riding, Horseshoes, Kayaking, Sailing, Shopping, Sight-seeing, Swimming, Tennis courts, Tennis racket rental, Water sports

Check Dates Visit Website


  • Check In:: 3 pm-7pm
  • Check Out:: 12 noon
  • 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 Two pet friendly rooms
  • Disabled Access Limited

Terms and Conditions

  • Minimum Stay: Holidays, Saturdays in Season, two night min. Call for exceptions
  • Accepted payments Other, AMEX, VISA, Discover, Mastercard, Personal checks, Travelers checks, Cash
  • Deposit Amount Required: One night deposit will be charged to your credit card two months prior to your arrival. 50% for 3 or more nights.
  • Cancellations: Cancellation must be made no later than 14 days prior to your arrival date. Cancellation made after 14 days, will be charged one night's rate at the highest rate to your credit card. If your accommodations can be resold, a $25 cancellation fee will replace the one night rate cancellation mentioned above. There is a $25 fee no matter when you cancel



Scott and Kaylin Benfield

Languages spoken


Resident Pets


About the innkeepers

Scott and Kaylin come to us from Philadelphia where they spent the last seven years experiencing the city of brotherly love. Scott has a background in hospitality and has managed hotels and restaurants in New York and Philadelphia. Kaylin has design, marketing and sales experience and has worked for various promotional marketing companies. As a couple and with their dog Molly of course they look forward to their new home in Chestertown and experiencing what the Eastern Shore has to offer. It is

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Full buffet with hot entree

  • Time Served: 8:30 am to 10:30 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.