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Great Oak Manor

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309 Reviews from our TripAdvisor Community

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Showing 309: English reviews
Blue Bell
Level Contributor
5 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed 1 week ago

This place is a hidden gem, the property is breathtaking , at the waters edge. The building itself is magical when you drive up the tree lined driveway. Every room is updated and unique. We were there as a family of 6 this past weekend. Mike went above and beyond to accommodate all of us. Lynn was delightful upon check... More 

Helpful?
Thank frequentflyer3343
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

Thank you for taking the time to write a review! We appreciate all feedback we receive and we are so happy your family enjoyed the visit! Come back soon and take care! Mike More 

Reisterstown, Maryland
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
INNKEEPER’S FAVORITE REVIEW
5 of 5 stars Reviewed July 3, 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?
1 Thank Michelle Y
About Innkeeper's Favorite Review
The Innkeeper’s Favorite Review is a recent traveler review pinned as a favorite by this property’s owner or manager.
Lititz, Pennsylvania
2 reviews
5 of 5 stars Reviewed 1 week ago

Great place to visit if you're looking for real privacy in a B&B atmosphere. Beautiful view of the Chester River. Complimentary continental breakfast was very nice and innkeepers were accommodating. Ideal romantic spot for couples, but not for children and far away from restaurants and attractions.

Helpful?
Thank Kellw622
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

You are so right right when you say Privacy! Great Oak Manor is a space where everyone can enjoy the peace and quiet! Breakfast is the only part of the day that can get crowded.. Thank you for the review and we look forward to a return visit! Mike More 

West Chester, Pennsylvania
1 review
5 of 5 stars Reviewed 2 weeks ago

We thoroughly enjoyed our weekend stay at Great Oak Manor! We loved our comfortable and quaint suite with modern amenities, the great breakfasts, kayak paddling and bicycling! The manor is impressive (loved the library!) with an interesting history and we got great dinner recommendations to restaurants in Chestertown, MD.

Helpful?
Thank Hummingbird860
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

Hello and thank you for the great review! Giving out Restaurant advice is hard for me, I would feel terrible if your experience wasn't five star! I always say the local hangouts are the best! Until we see you again, Take care! Mike More 

1 review
5 of 5 stars Reviewed 2 weeks ago via mobile

Me and my wife Margaret came to Great Oak Manor for our annual mini vacation over Memorial Day Weekend and it was by far the greatest trip we've had yet. I must admit that I was very reluctant when my wife suggested visiting a small bed and breakfast in the middle of nowhere for our three day mini vacation(I normally... More 

Helpful?
Thank GregSterling68
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

Thanks Greg for staying with us at Great Oak Manor and for the review, As I have read over reviews to learn what and how we can improve its nice to hear from first time guest about the property. Glad you had a great experience and we look forward to seeing you again soon.. Mike More 

Philadelphia, Pennsylvania
1 review
3 of 5 stars Reviewed 2 weeks ago

This was our second time visiting Great Oak Manor (first was for Valentine's Day 2016) and we were rather disappointed in what has become of the B&B. Scott and Kaylin Benfield were the inn keepers during our first visit and they were absolutely wonderful. They were always around, interacting with the guests, and offering food and wine throughout the day.... More 

Helpful?
Thank shancran11
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

I'm sorry you feel this way about the improvements here at Great Oak Manor, I did offer you to join other guests that had ordered a crab feast that includes Crab, Shrimp, Potatoes, corn on the cob, beverages and dessert. We feel this is a great deal as the cost of fresh seafood varies from time to time. We are... More 

1 review
1 of 5 stars Reviewed 3 weeks ago via mobile

the view was great, the service/food/stay was not. Inn keeper was a little unprofessional. Staff was hard to find after 6. There wasn't a lot of privacy. Room smelt of smoke and pets. Toilet was hard to flush. Had better experiences at motel 6.

Helpful?
Thank Shipyard123
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

Shipyard123, I encourage you to contact us directly so that we may understand your experience to ensure that this would never happen again. We try very hard as you can tell by most reviews to make sure everyone has a pleasant experience. We do have many things we take care of around the manor inside and the grounds outside so... More 

Washington DC, District of Columbia
Level Contributor
3 reviews
5 of 5 stars Reviewed 3 weeks ago

My wife and I were looking for a quiet mid-week getaway. I stumbled upon this gem on the eastern shore. The house was nice, private, quiet and large. The grounds are beautiful with plenty of things to do, such as cornhole. We were able to just kick back and watch the sunset, which is an absolute MUST. In the morning... More 

Helpful?
Thank cavanaughfs
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

Tesla and many Select Registry properties have teamed up to offer chargers at many great locations. We are so glad you chose Great Oak Manor for a wonderful getaway! Hope to see you back again soon! Mike More 

1 review
5 of 5 stars Reviewed 3 weeks ago

I stayed with my family for a weekend and was ultimately impressed. There are amenities that will keep you busy for days with picturesque views all around. What made the stay so enjoyable was Mike. He embodied a homey, friendly spirit and was the closest I have come to perfect customer service. Mike will make sure you have everything you... More 

Helpful?
Thank Jason D
Mikeatgreatoak, Owner at Great Oak Manor, responded to this review

Your kind words about the staff and Great Oak Manor are very nice and much appreciated! Stay tuned to our website for the newest of amenities and other exciting news here at Great Oak Manor! Mike More 

Philadelphia, PA USA
Level Contributor
15 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed 3 weeks ago

I stayed at Great Oak Manor for a blissful three days with my dog so we could have a quick escape from urban madness. It was PERFECT. Quiet and serene, I could choose to just sit on the grounds with a cocktail and listen to the birds and water, or be active and swim/kayak/bike...or drive 15 minutes into town for... More 

Helpful?
Thank phillyqueenie
Mikeatgreatoak, General Manager at Great Oak Manor, responded to this review

Thanks so much for your amazing review, we love our four legged friends and arre so happy you chose Great Oak Manor.. See you soon! Mike More 

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Amenities

Highlights
  • Free Parking
  • Free Breakfast
  • Beachfront
  • Bar/Lounge
  • Free High Speed Internet ( WiFi )
GreenLeadersGold level
About the property
  • Beachfront
  • Non-Smoking Hotel
  • Pets Allowed ( Dog / Pet Friendly )
Things to do
  • Bar/Lounge
Room types
  • Non-Smoking Rooms
  • Family Rooms
  • Suites
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 21620-4115
Location: United States > Maryland > Chestertown
Price Range: $175 - $296 (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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