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Great Oak Manor

Orbitz.comUSD 269*
View Deal
Certificate of Excellence
GreenLeadersGold level
11/06/2017 12/06/2017
1 room 2 adults 0 children
USD 309*
USD 269*
USD 309*
USD 309*
USD 269*
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Great Oak Manor
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346 Reviews from our TripAdvisor Community

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Showing 346: English reviews
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Denver, Colorado
Reviewed 2 days ago NEW

The Georgian style manor is situated on lovely wooded grounds right on the Chesapeake Bay with a sandy beach and marina a short walk from the property. Watching the sun set over the bay from the adirondack chairs on the yard was special. Inside, the manor is a mix of elegance and relaxation from the common areas to the cozy...

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Helpful?
Thank Al B
Reviewed 3 days ago NEWvia mobile

Everything you could need is on this serene estate...kayaking, biking, reading, etc. Also learned some history of the property and explored the area. We had a very relaxing stay and a delicious breakfast! Would definitely recommend Great Oak Manor!

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Thank haylr13
Phoenixville, Pennsylvania
Reviewed 2 weeks ago

My wife and I have stayed at the Manor numours times over the past 30 years and our last experience was by far the most enjoyable. The Manor has always been a beautiful destination with a marvelous estate house and accommodations. The long suit this time was the atmosphere provided by the inkeepers, Holly and Richard. All the amenities were...

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Helpful?
Thank morgand1233
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you very much for your kind words. We so appreciate our return guests and are thrilled to hear your last visit exceeded your expectations. We look forward to your next visit.

Brunswick, Maine
Reviewed 3 weeks ago

Great Oak Manor evokes the feel of gracious living in a bygone era. We relaxed in sun-filled common rooms, large and small, and enjoyed delicious breakfasts in the pleasant dining room. But it was the beautifully landscaped grounds, with many outdoor seating options on the acres of lawn overlooking Chesapeake Bay, that meant the most to us. We traveled from...

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Helpful?
Thank dvail04011
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

We are so glad to hear how much you enjoyed yourselves on this beautiful property. We are working to upgrade all of our rooms; it just takes time. Perhaps next time you can stay in the latest renovated room. We thoroughly enjoyed having your family for breakfast and hope they will join us next time too.

Washington DC
Reviewed 3 weeks ago via mobile

A very nice property on the Bay about seven miles outside of Chestertown. Features well-appointed and large rooms, friendly and responsive innkeepers, lovely grounds, and excellent breakfasts. An extra benefit: beautiful sunsets over the Bay.

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Thank Emmett4640
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Yes, it is those amazing sunsets over the Bay that brings us back, isn't it? We love it when our guests thoroughly enjoy themselves and the Manor.

Oley, Pennsylvania
Reviewed 5 weeks ago

Everything about this establishment is first class, and the fact that they have dog-friendly rooms is fantastic! The room has access to an outdoor garden area so you don't disturb other guests. I can't say enough about the friendliness of Holly, Richard and the entire staff at Great Oak Manor. The peaceful beauty of the sunset, water, private beach, and...

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Helpful?
Thank cbeenjammin
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Wow! Thank you for those wonderful words of praise for Great Oak Manor. We love our pets here so we hope you will visit with yours again real soon. Holly

Reviewed 23 April 2017 via mobile

Always love staying at the Great Oak Manor, especially this past 2-day visit as innkeeper Holly went way out of her way to accommodate my special dietary needs. She made delicious breakfasts for me each day and passed on to me her recipe for the best granola I've ever tasted! We plan on returning as soon as possible as Holly...

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Helpful?
Thank 1slowdancer
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you for your kind words. We loved having you and don't mind a bit helping out anyone with special dietary needs. I am so grateful you enjoyed my offerings. I hope you have made the granola and are enjoying it at home. Hurry Back!! Holly

Swarthmore, Pennsylvania, United States
Reviewed 16 April 2017

My first bed and breakfast and now I'm spoiled. Beautiful, serene, property right on the water! The Inn was fabulous from the room accommodations, the staff, the food and the overall atmosphere. Kayaking, bike riding, and relaxing on the hammock by the water make this an outstanding place to stay. I stayed in the Caulk room which was much better...

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Thank Cheryl P
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you Cheryl. We are so glad you first bed and breakfast experience was such a good one. We are looking forward to having you and Shana visit again. Holly

New York City, New York
Reviewed 10 April 2017

Simply outstanding B&B on the shores of the Chesapeake Bay, including - excellent hospitality from innkeepers Holly & Richard, thoughtful touches of unique services from breakfast through evening snacks & drinks to well-maintained common rooms and facilities. Grounds were in excellent shape as well, including access to private beach. Very enjoyable visit even with a cool spring day keeping us...

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Helpful?
Thank Kevin G
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you Kevin. It was such a pleasure having you and Kristin stay with us. It thrills us to see our guests use the property and the access to the Bay. We look forward to you next visit. Holly

Reviewed 10 April 2017

This is a wonderful location, right on the Chesapeake Bay on the Eastern Shore. The sunsets and views are spectacular and the setting can put your worries out of mind. The proximity to Chestertown, truly a hidden treasure with centuries of history and a thriving arts community, and to the Eastern Neck Wildlife Refuge, which is a great place to...

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Helpful?
Thank Pennymohr
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you Penny for your thoughts. Your points are well taken. Currently we serve breakfast between 9-10, soon to change to our summer hours of 8:30-10. It is a problem when everyone shows up at once on occasion. We had a full house this weekend but had nicer weather so many people chose to have breakfast on our patio facing...

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11/06/2017 12/06/2017
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Amenities

Highlights
  • Free Parking
  • Breakfast included
  • Beachfront
  • Free High Speed Internet ( WiFi )
GreenLeadersGold level
About the property
  • Beachfront
  • Pets Allowed ( Dog / Pet Friendly )
  • Non-Smoking Hotel
Room types
  • Suites
  • Non-Smoking Rooms
  • Family Rooms
In your room
  • Air Conditioning
Internet
  • Free High Speed Internet ( WiFi )
  • Free Internet
Services
  • Free Parking
  • Breakfast included
Official Description (provided by the hotel)
Great Oak Manor is located on Maryland's Eastern Shore, where the Chesapeake Bay is aglow in vibrant, warm sunsets; where towering oaks gently kiss the skyline; and where you can let your body rest and your mind wander. Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the Chesapeake Bay waterfront. With 12 guestrooms and various common rooms, Great Oak Manor offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night. Whether you're adventurous, need to get away, or just want to be taken care of, there's something here for everyone. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck Refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view. Aside from offering a relaxing getaway for travelers, Great Oak Manor also serves as the ideal location for various events, retreats, parties, and weddings. Welcome to our home, stay a while. ... more   less 

Additional Information about Great Oak Manor

Address: 10568 Cliff Rd, Chestertown, MD 21620-4115
Region: United States > Maryland > Chestertown
Price Range: $352 - $475 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 12
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Also Known As:
Great Oak Manor Hotel Chestertown
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Questions & Answers

Here's what travellers have asked, with answers from Great Oak Manor staff and other travellers.
3 questions
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Columbia, Maryland
Ocean City, New Jersey
1 month ago

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Questions? Get answers from Great Oak Manor staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travellers prefer

“Bay views from rooms along the back of the manor”
alb970, 26 May 2017 | Read review
“Ask for a bay view room”
dvail04011, 6 May 2017 | Read review
“They do have dog-friendly rooms available.”
cbeenjammin, 23 Apr 2017 | Read review
“the website does not do the rooms justice. All have a little different flair.”
  • caulk room
846CherylP, 15 Apr 2017 | Read review
“Geddes Piper is charming! But I'm sure they are all awesome!”
kristins786, 9 Apr 2017 | Read review
5 of 5
Orbitz.com
USD 269* /night
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Booking.comUSD 309
TripAdvisorUSD 269
CheapTicketsUSD 269
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*Disclaimer
Prices are for 1 room, 2 adults
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