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Great Oak Manor

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Great Oak Manor
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341 Reviews from our TripAdvisor Community

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Showing 341: English reviews
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Oley, Pennsylvania
Reviewed yesterday NEW

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
Reviewed 2 days ago NEWvia 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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Thank 1slowdancer
Swarthmore, Pennsylvania, United States
Reviewed 1 week ago

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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Helpful?
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 2 weeks ago

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 2 weeks ago

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...

Gardners, Pennsylvania
Reviewed 2 weeks ago

The place is absolutely gorgeous! Extreme old-world charm in every room. The 'conservatory' was my favorite place to watch the bay. Holly and Richard are doing a wonderful job - you would never know they just arrived themselves a few short weeks ago! This is one place that I will definitely want to return to in the future. Lizzy is...

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

Thank you Kristin. It was a pleasure having you and Bill with us. Sure hope you will come again and visit us and Lizzie. Holly

Washington DC, District of Columbia
Reviewed 2 weeks ago via mobile

We spent two nights in this beautiful B&B. The rooms are spacious and clean. There are several common areas rooms where you can spend sometime relaxing. The library is cozy and the innkeepers encouraged us to start a fire. You can sip some liquor , offered by the innkeepers, and relax in front of the fire . There is also...

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Helpful?
Thank Sabaudia10
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

Thank you for your lovely remarks. We want all of our guests to feel at home when they visit and to enjoy the Manor as much as possible. The Chesapeake Room, which is the den/bar area of the house is stocked all the time with soft drinks, coffees, teas, cereals, popcorn, snack bars, etc. I hope you were shown this...

Reviewed 2 weeks ago via mobile

Wonderful experience! Planned a private party for my sweeties retirement and I could not have asked for a better location.Holly , the Inn keeper was so helpful and kind. They had a masseuse come to the room and give us a couples massages.Then a private dinner in the room.The food was 5 star, especially the bread pudding with bourbon sauce....

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

It was so much fun for us to help make your surprise happen. You had planned a perfect weekend and we were honored we could help make it happen. We hope you will come again. Holly

djk_9
Reviewed 3 weeks ago

My husband and I spent one night last weekend in a room right in the middle of this gorgeous b&b manor, overlooking the Bay. The room was impeccable, the slumber luxurious, the owner very friendly.....she first gave a a tour of this beautiful Inn. Breakfast was very good quiche, juice, coffee, asparagus, fruit. All the guests were very friendly too....

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Thank djk_9
GREATOAKMANOR, Manager at Great Oak Manor, responded to this review

We are so glad you had a wonderful experience in this beautiful part of the Eastern Shore. There is so much to see and do or to do nothing and just sit and watch Mother Nature work her magic on the Bay. We hope you will return for a longer stay. Holly

Fair Haven, New Jersey
Reviewed 4 weeks ago

We were very impressed with the magnificent rooms in the Manor. The view of the water was great. We managed to catch the sunset that evening. Vincent told us we could have a fire in our room, so we did. It was cozy and warm and very comfortable. Unfortunately we were getting blizzard warnings for the following day so we...

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Helpful?
Thank Kathy W

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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 Internet
  • Free High Speed Internet ( WiFi )
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
Region: United States > Maryland > Chestertown
Price Range: $255 - $440 (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
17 days 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

“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
“Ask for a water view, although you probably will enjoy the grounds one way or the other.”
djk_9, 3 Apr 2017 | Read review
“Some rooms have a view of the water.”
Q1116OYkathyw, 22 Mar 2017 | Read review
5 of 5