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Great Oak Manor

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

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About

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.

Reviews

Overall
4.5

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  • Guest room4.5
  • Service4.7
  • Value4.2
  • Cleanliness4.6
  • Onsite Dining4.5

Score Breakdown based on
86 Reviews

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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.


A unique place

5 on May 04, 2012

My wife and I stayed at the Manor in April 2012. Know what you are looking for: this is a somewhat remote, beautiful, serene gorgeous place. No miniature golf, no neon, no nonsense. But "Wow!" Just beautiful. On the Chesapeake Bay. With, incidently, beautiful Persian rugs.


It was a perfect pick!

5 on February 28, 2012

Although it was only for 1 night, it was the perfect stay. We were greeted when we drove up by Cassandra and Charlie (tail wagging) and I immediately felt at home. After a tour of their beautiful home, showing us where everything was. Our room was beautiful and after settling in were spoiled by a nice tray of cheeses and fruit before heading out to dinner. After a great meal in Chestertown, we came back to our room and enjoyed the fireplace in our room and quiet time. We awoke to a beautiful view outside our room of the river and enjoyed a wonderful breakfast with eggs and fresh blueberry muffins. Excellent service and hospitality. Thanks to all for making our short stay a memorable one!


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Rooms & Rates

D'Oench

Deluxe waterfront room with handsome finishes, such as crown molding and a grand fireplace, that compliment the panoramic views of the bay. The room boasts a king size bed, reading chairs, a gracious bath, and a name that comes from the first owner of the house.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $249 - $315

Nightly Rate: $249 - $315

Roese Suite

Deluxe two room suite with a separate living room with fireplace, a stately bedroom with king bed, and spacious bath with skylight. Enjoy garden and courtyard views from the windows. Conveniently located near the Conservatory, this suite serves as one of our two dog friendly rooms.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $249 - $315

Nightly Rate: $249 - $315

Hodges

Charming Estate view room with a stately queen size poster bed, a gorgeous fireplace, private bath, and cozy chairs for reading. This room has a great view of the boxwood garden.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $179 - $269

Nightly Rate: $179 - $269

The Marmaduke

Rise to breathtaking views of the bay from a king-sized bed that begs you to stay under the covers for a moment longer. Bright and airy, the Marmaduke features rich floral hues and chairs perfect for reading or gazing at the view. With a cozy fireplace, walk-in closet and sumptuous bath with soaking tub, this luxury guest room is as lovely as the first land owner for which it is named.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $249 - $315

Nightly Rate: $249 - $315

The Wickes

Rekindle a romance in front of a roaring fireplace in a room that overlooks the grounds of our magnificent estate. Named for Captain Lambert Wickes, skipper of the 16-gun sloop that carried Benjamin Franklin to France, this room features a king-size bed, a walk-in closet, and a large, private bath. Crown molding and chair rails, built-in bookcases, reading chairs, and paintings of sailboats add just the right finishing touch.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $179 - $269

Nightly Rate: $179 - $269

The Tylden

With an Oriental Mural, think of it as Georgian meets Asian fusion. The king-size bed with feather topper is the perfect place to curl up and read a book as you gaze out at the bay. A small area outside the door is a great place to watch the sun set over the bay. The private bathroom features a stand alone shower.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $179 - $269

Nightly Rate: $179 - $269

The Geddes-Piper

There’s something about this room that makes you feel right at home. Nestled away on the third floor, this intimate place boasts an interior balcony where you can watch the boats go by on the bay, and a fine collection of black and whites from photographer, Marion E. Warren. The Geddes-Piper room boasts a king-size bed and a private bath.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $229 - $269

Nightly Rate: $229 - $269

The Russell

Named for Great Oak’s most notable gamer, the Russell Room boasts a plush lounge area, a large television, a fireplace, and a large bath. This majestic room has an old boy’s club feel with a softer side. Rich reds, plaids, and mahogany walls are downplayed by the oriental rugs and crisp linens. Let the games begin.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $249 - $315

Nightly Rate: $249 - $315

The Ringgold

Comfort knows no boundaries in the graceful Ringgold room, which possesses a king bed, a full bath, and cottage-style comfort. The Ringgold truly feels like your home by the sea;or in this case, the bay.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $159 - $200

Nightly Rate: $159 - $200

The Caulk

Named for the Caulk battlefield and the only battle fought on the Eastern Shore in the War of 1812, this room is filled with history. The water calls to you from your own private lookout over the Chesapeake. Enjoy this spacious room with a private bath that boasts walls the color of the sunsets, an inviting, rich red.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $249 - $315

Nightly Rate: $249 - $315

The Hynson

The Hynson possesses the charm of a French country cottage, with the comforts of an estate home in Provence. Look out a dormer window to find inspiring views of the water and the grounds of the estate. The Hynson also features a private bath.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $165 - $200

Nightly Rate: $165 - $200

Platinum

Deluxe waterfront rooms with fireplace and king size bed and private bath. All rooms have TV, DirecTV, WiFi, and phone.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $249 - $315

Nightly Rate: $249 - $315

Gold

Waterfront or Estate view rooms with king size bed and private bathroom. All rooms have TV, DirecTV, WiFi, and phone.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $179 - $269

Nightly Rate: $179 - $269

Silver

Charming third floor rooms with king size beds, private baths and dormer windows. All rooms have TV, DirecTV, WiFi, and phone.

  • Maximum Capacity: 2
  • Bathroom Private Bath

Nightly Rate: $165 - $200

Nightly Rate: $165 - $200

Sterling Suite

This lovely first floor suite has french doors from the bright sunny bedroom to the Manor's courtyard garden. This is also one of our pet friendly rooms.The living room is where you can curl up with a good book on the pull-out sofa or watch TV. The private bathroom has a large walk in shower.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $179 - $269

Nightly Rate: $179 - $269

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Location

Location Type

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

Airport

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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Policies

  • 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

Innkeepers

Name(s)

Jenn Donisi

Languages spoken

English

Resident Pets

Dogs

About the innkeepers

The best part of being an Innkeeper? The guests. They always bring such unique backgrounds and stories with them. The people always make this job worth it.

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Meals

Breakfast

Full buffet with hot entree

  • Time Served: 8:30 am to 10 am
  • Serving Location: waterside terrace, Dining Room

Special meal options

Low fat , Restrictive , Vegetarian , Inquire upon booking


Signature Dish

Crab Quiche
Our Breakfast buffet has seasonal fresh fruit, homemade muffins and breads, cold cereal, yogurts and a hot entree'. Depending on the day, you may be served either French toast and sausage, crab quiche or quiche Lorraine, eggs and ham to order, your preference, or an egg strata.


Recipes

Deals


Special Package

Last Minute Weekend Special

Weather this weekend is going to be beautiful and we want to give you an excuse to getaway and enjoy it on the Chesapeake Bay. We're offering 25% off when you call to book a reservation to stay with us during this weekend, April 17-19. Offer cannot be combined with other specials or discounts.

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Details

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

Property highlights


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