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Great Oak Manor

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GreenLeadersGold level
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10568 Cliff Rd, Chestertown, MD 21620
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289 Reviews from our TripAdvisor Community

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There are newer reviews for Great Oak Manor
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Showing 289: English reviews
Drums, Pennsylvania
2 reviews
5 of 5 stars Reviewed June 19, 2016

Elegance and comfort in beautiful B&B . Formal music room and library ; huge conservatory overlooking Bay. TV room and kitchen for guests. Bedrooms spacious, clean, beautifully decorated; beds very comfortable. Breakfasts creative and delicious. Spent evenings on lawn under towering trees watching unforgettable sunsets. Will definitely return.

Helpful?
Thank Janice W
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Janice, We are so pleased to know that you enjoyed your stay and were able to take advantage of our beautiful grounds and scenic view. Thank you for your kinds words about our breakfast, we aim to please! We do hope to see you back again soon. Kaylin Benfield, Innkeeper More 

Alexandria, Virginia
Level Contributor
3 reviews
5 of 5 stars Reviewed June 18, 2016

Outstanding in all categories. The breakfasts are a delight, and full of surprises. It is remote enough to be out of the beaten path, but close enough to Chestertown and Rock Hall to enjoy equally outstanding dinners. There is a friendly and helpful staff if you should need anything. The rooms are of equally high standards. It would be difficult... More 

Helpful?
Thank ellshipmodeler
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Gene, we are so pleased that you enjoyed your stay and found the Manor to be such a perfect location for your get-away. We pride ourselves on service and thank you for your kind words. We do hope that you will join us again soon! Kaylin Benfield, Innkeeper More 

Bethesda, Maryland
1 review
5 of 5 stars Reviewed June 13, 2016

This gem of a bed and breakfast gets extra points for being pet friendly. Beautiful views in every direction - and two hammocks to choose from! The breakfast was amazing, and fortified me for the entire day. Would definitely put the Great Oak Manor at the top of my list next time Chestertown beckons.

Review collected in partnership with this hotel

Helpful?
Thank betsy s
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Betsy, we love having four legged friends on property and are so happy that you enjoyed our great property with yours. We certainly do hope that the next time your in the Chestertown area you will come and join us again! Kaylin Benfield, Innkeeper More 

Springfield, Virginia
Level Contributor
58 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 25 helpful votes
5 of 5 stars Reviewed June 10, 2016

9 June 2016 - More than Excellent, this B&B is Outstanding. Upon arrival we were greeted by the Inn Keepers and immediately given a tour of the house and grounds even before checking-in. We were impressed with how clean everything was and the attention to detail of everything. The Manor has been restored with quality products and quality work; ceiling... More 

Helpful?
Thank WaltOkon
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Walt, we are so happy to hear that both you and Rosie enjoyed your stay! We certainly take pride in the amenities that we offer and love when our guests can take advantage of them. We enjoyed having you both as our guests and do hope that you will com and visit us again soon. Kaylin Benfield, Innkeeper More 

Alexandria, Virginia
1 review
5 of 5 stars Reviewed June 7, 2016

My husband and I had our wedding weekend celebration at Great Oak Manor. We held a Friday night ceremony on the bluff on the expansive lawn of Great Oak overlooking the Chesapeake. This was followed by dinner and dancing as well as an all day party the next day. Every detail was perfect. The Manor House was a great place... More 

Helpful?
Thank pjburch2104
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Pam, thank you so much for your kind words. It was such a pleasure to host your special day and be a part of such a wonderful event! What a fabulous weekend of families coming together to celebrate. We wish you all the best and look forward to having you back as our guests soon! Kaylin Benfield, Innkeeper More 

Philadelphia, Pennsylvania
1 review
5 of 5 stars Reviewed June 6, 2016

A wonderful place to get away and enjoy the beautiful surroundings by doing as little or as much as you want with great rooms. The kayaks, beach, chickens, birds, bikes, and toad's all made it a beautiful natural getaway for couples or families.

Review collected in partnership with this hotel

Helpful?
Thank Jennifer S
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Jennifer, we are so happy that you were able to enjoy all of the amenities and even the wild life that the property has to offer. It was a pleasure to host yourself and your family and we do hope you'll come back again soon. Kaylin Benfield, Innkeeper More 

Fairfax, Virginia
1 review
5 of 5 stars Reviewed June 6, 2016

We loved our stay at the Great Oak Manor, a beautiful property with an excellent staff. We went with our four legged companion and two kids.Breakfast was great, ready to accommodate a small request for a picky toddler . When we arrived, our room was ready with a bowl of water for our doggy which it was so thoughtful.

Review collected in partnership with this hotel

Helpful?
Thank mcaldwelva
GOMStaff, General Manager at Great Oak Manor, responded to this review

We are so pleased to hear that you enjoyed your stay at the Manor, it was a pleasure having you all! You had a beautiful weekend of weather to enjoy, we do hope that you will come and visit again soon. Kaylin Benfield, Innkeeper More 

Philadelphia, Pennsylvania
1 review
4 of 5 stars Reviewed June 3, 2016

To be fair, our stay was too short to give a detailed review. However, the inn keepers were both very friendly and helpful. The breakfast and afternoon snack were delicious. We had read the the food was good and it is one of the reasons we chose to stay at Great Oak Manor.

Review collected in partnership with this hotel

Helpful?
Thank A8457REericb
GOMStaff, General Manager at Great Oak Manor, responded to this review

Although your stay was brief we are so happy to know that you enjoyed the property and food. We certainly hope that you might come and visit us again for a more extended stay! Kaylin Benfield Innkeeper More 

West Chester, Pennsylvania
1 review
5 of 5 stars Reviewed June 2, 2016

We just loved our stay at Great Oak Manor! Kaylin and Scott were most gracious Innkeepers. They made us feel at home right away. We had our dog, Sophie, with us and they made her feel at home, also! The Inn is beautiful and our room was spectacular. Breakfast was delicious and we loved sitting at the water's edge watching... More 

Review collected in partnership with this hotel

Helpful?
Thank spikew1
GOMStaff, General Manager at Great Oak Manor, responded to this review

Thank you so much for your kinds words, it was a pleasure to have you both as well as Sophie as our guests! We are so pleased that you enjoyed your stay and plan to make a return visit, we look forward to seeing you then. Kaylin Benfield Innkeeper More 

2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 1, 2016

The Manor had everything we needed for a relaxing retreat. When we arrived there were deer on the lawn, bald eagles and ospreys flying above us. The breakfasts were homemade and delicious, the bay was beautiful and easy to explore on the inns paddle boards, and the beds were unbelievably comfortable; we haven't had that much sleep in years!! Every... More 

Review collected in partnership with this hotel

Helpful?
Thank SarahinFulham
GOMStaff, General Manager at Great Oak Manor, responded to this review

Hi Sarah, It is so great when our guests are able to take advantage of the properties amenities like the paddle boards and explore the gorgeous Bay! We are thrilled to know that you enjoyed your stay and got some well deserved rest and relaxation. Kaylin Benfield Innkeeper More 

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Amenities

Highlights
  • Free Breakfast
  • Beachfront
  • Free Parking
  • Bar/Lounge
  • Free High Speed Internet ( WiFi )
GreenLeadersGold level
About the property
  • Beachfront
  • 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 Breakfast
  • Free Parking
  • 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
Location: United States > Maryland > Chestertown
Price Range: $188 - $287 (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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