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Great Oak Manor

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321 Reviews from our TripAdvisor Community

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Showing 321: English reviews
Reisterstown, Maryland
Level Contributor
4 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
Reviewed 5 days ago NEW

This is our second stay at Great Oak Manor but it felt like we were coming home. Mike, Lynne and Bill, thank you again for an amazing get-a-way! We enjoyed 3 nights in the D'Oench room (second floor). The views are stunning and the room spacious with a real fireplace. The bed is incredibly comfortable yet firm enough that you... More 

Helpful?
1 Thank Michelle Y
Reisterstown, Maryland
Level Contributor
4 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
INNKEEPER’S FAVOURITE REVIEW
Reviewed 3 July 2016

Between Vickie Cunningham and Innkeeper Mike Sorrels our stay was pure enjoyment, as a matter of fact we loved it so much we stayed an extra night!! Hospitality is amazing, attention to detail is exceptional. The staff is hardworking and attentive and the grounds are immaculate. From the moment we walked through the front door we felt completely welcome. If... More 

Helpful?
3 Thank Michelle Y
About Innkeeper's Favourite Review
Level Contributor
4 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
Reviewed 5 days ago NEW via mobile

We stayed in the Russell room Thanksgiving Day weekend and we couldn't have left more relaxed. The breakfast Mike provided was excellent the grounds were great the local restaurants were terrific especially the Bay Wolf the room was fantastic the history interesting the staff was courteous and professional

Helpful?
1 Thank rockborn s
Easton, Pennsylvania
2 reviews
Reviewed 1 week ago

We had stayed at this property before and were looking forward to another wonderful stay. Unfortunately, our experience on this visit left a lot to be desired. The location is wonderful, but that is where it ended. The inside of the building needs quite a bit of renovation, from very worn rugs, to painting of moldings to wallpaper coming off... More 

Helpful?
Thank RoHoehler
Pikesville, Maryland
Level Contributor
15 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
Reviewed 3 weeks ago

Right on the water, large property, well kept. It's as good on the inside as it looks on the outside. Elegant and classy with the most excellent staff we have encountered. Breakfast was great, our evening dinner on Friday a very pleasant surprise. More to do just around the Manor than we had time for, very highly recommended!

Helpful?
Thank F21208
Mohnton
Level Contributor
33 reviews
16 hotel reviews
common_n_hotel_reviews_1bd8 14 helpful votes
Reviewed 27 October 2016

The property is excellently maintained and the grounds are beautiful. Bikes and kayaks are free to use. While the inn's furnishings are formal, the feel is more casual in the dining area with a beautiful sun room that looks out over the lawn and river. Mike is very accommodating and professional as the innkeeper and quickly takes care of requests.... More 

Helpful?
1 Thank Bob W
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

Thank you for taking the time to review our Manor. We are so pleased that you enjoyed the grounds with the beautiful views along with our amenities. We agree, the carriage house is spectacular and is a must see! We look forward to having you back. Thanks, Mike More 

Philadelphia
Level Contributor
38 reviews
20 hotel reviews
common_n_hotel_reviews_1bd8 32 helpful votes
Reviewed 20 October 2016

Beautiful place. We loved having use of the kayaks for the whole afternoon our first day. They were very kind to let us use them a bit early and provided great advice as to where to find lunch and dinner in the off season. The grounds very beautiful and well kept. Breakfast was delicious, homemade. The afternoon snacks and port... More 

Helpful?
Thank marston258
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

Thanks for staying with us and for your review. We are so glad that you enjoyed our manor, grounds and amenities. We couldn't agree more that an afternoon on the kayaks is a great start to a getaway. We are sorry for the inconvenience with the wifi, we have put a lot of thought into this are will continue to... More 

Fairfax, Virginia
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
Reviewed 18 October 2016 via mobile

Two years since first visit when we were first guest of a new own. It was fun then and now even better. Perfect place for a getaway with wildlife parks nearby and a small town historical center with a nice walking tour. Don't miss din din at The Blue Heron.

Helpful?
Thank Kenneth C
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

We are so glad that you enjoyed your most recent visit to the manor and love to hear that it was even better than your last time here. We agree that historic Chestertown is an amazing place to wander around. We look forward to your next visit. Thank you, Mike & Lynne More 

Manalapan, New Jersey
Level Contributor
14 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 19 helpful votes
Reviewed 18 October 2016

My husband and I spent last weekend with friends at the Manor. The innkeeper Mike and the assistant Innkeeper Ryan did everything to make sure the guests were treated to a wonderful experience. The view of the Bay was unbelievable and the firepit and torches lit at night were the added touches that made this weekend special. The breakfast was... More 

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

We are so happy to hear that you enjoyed your recent visit with us. The views and the conversation around the fire pit are some of our favorite things about the manor too! We are also happy that you liked your breakfast service so much, we work hard at keeping it creative and delicious and are pleased to hear it... More 

Lititz, Pennsylvania
Level Contributor
8 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
Reviewed 17 October 2016

We can't say enough positive about our recent stay at Great Oak Manor. The manor itself is absolutely lovely with tasteful furnishings in every room. We enjoyed strolling the grounds, sitting on the Adirondack chairs watching the gorgeous sunsets over the bay, and relaxing with a complimentary glass of port at the end of the day. The breakfasts were outstanding... More 

Helpful?
Thank triscuit2015
GREATOAKMANOR, General Manager at Great Oak Manor, responded to this review

Thank you for the great review, we are happy to hear how much you enjoyed the manor and it's gorgeous furnishings, beautiful grounds and delicious breakfasts. It is definitely a great place to getaway and relax. We look forward to your next visit. Thank you, Mike & Lynne More 

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Amenities

Highlights
  • Free Parking
  • Free Breakfast
  • 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
  • Free Breakfast
  • Meeting Rooms
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: $235 - $345 (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.
2 questions
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Columbia, Maryland
Ocean City, New Jersey

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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

“Do not book a room on the third floor. Too far up and in need of updating.”
 of 5 bubbles RoHoehler, 20 Nov 2016 | Read review
“D'Oench is a large room with a good view but no balcony. Caulk has the same view, it's a little smaller but has a small balcony area.”
 of 5 bubbles BobW60, 27 Oct 2016 | Read review
“Russel room fantastic”
 of 5 bubbles chemistandnurse, 18 Oct 2016 | Read review
“Every room is beautiful”
 of 5 bubbles frequentflyer3343, 14 Sep 2016 | Read review
“Best with view of Chester River.”
 of 5 bubbles Kellw622, 12 Sep 2016 | Read review
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