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

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!!!"

Great stay ar Great Oak

3.8 on August 19, 2012

My husband and I have been visiting Great Oak Manor for over 20 years. During that time the property has changes owners three times. It is always a pleasure to find that the lovely B&B stays as gracious and beautiful throught out the transitions. With beautiful rooms and friendly staff, rolling back lawns that meet the Chesapeake bay, hammocks and lounge chairs to sit in while one reads or watches the eagles and osprey fish, or puttering round Chestertown and near by Rock Haall, Great Oak Manor is a perfect get away, oh and yes, breakfast is yummy as well!

The Perfect Escape from the City!

4.8 on June 24, 2012

We experienced a beautiful weekend stay at the Great Oak Manor! It was the perfect venue for a quiet yet fun celebration for our anniversary and my birthday! The rooms are gorgeous and the complimentary breakfast is delicious! A great place to just BE.

Gorgeous manor home in a serene setting

4.8 on June 03, 2012

Meticulously maintained, beautiful decor in a beautiful setting. Outstanding service as well. The property is off the beaten path but a short drive to historic towns and other attractions.

A Great Get-Away

4.6 on May 27, 2012

My husband and I spent 3 nights at Great Oak Manor in May. We wanted a beautiful place on the water that was peaceful and quiet. And that is exactly what we had! The public spaces are elegant but comfortable. Breakfast was cooked to order every morning. We even saw a lovely sunset on the first evening. The staff was very friendly and extremely helpful. We will definitely go again!

Fabulous Place; Wonderful staff, food and views

4.8 on May 20, 2012

Stayed three nights with relaxation, friendly helpful staff and delicious breakfast. Definitely recommend.

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Rooms & Rates

Russell Suite

Our largest and most grandest room, runs the width of the mansion.

  • Maximum Capacity: 4


Beautiful waterview room with sweeping views of the Bay. Fireplace and bed that looks right out to the water, our most popular room.

  • Maximum Capacity: 2

Caulk Suite

Waterview Deluxe room with a small private sitting balcony. Garden interior theme with spectacular views of the bay.

  • Maximum Capacity: 2


Deluxe, waterview room that boasts a handsome interior

  • 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


Quaint waterview room with a standing only balcony and japan inspired interior

  • Maximum Capacity: 2

Geddes Piper

Third floor bedroom with a built in balcony that allows for a seating area with views of the bay.

  • Maximum Capacity: 2


Lovely estate view room with fireplace

  • Maximum Capacity: 2


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

  • Maximum Capacity: 2

Sterling Suite

Lovely 1st floor suite, handicap accessible, with french doors that lead out into the courtyard. Sofa bed.

  • Maximum Capacity: 4


3rd floor estate room with high ceilings

  • Maximum Capacity: 2


3rd floor room with high ceilings and a standing view of the bay

  • Maximum Capacity: 2


  • Maximum Capacity: 2


  • Maximum Capacity: 2

Dining Room

  • Maximum Capacity: 2

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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

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  • 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.