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Great Oak Manor

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10568 Cliff Rd, Chestertown, MD 21620
Special Price
August Mid-Week BOGO
Great Oak Manor
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Ranked #5 of 12 Chestertown B&B and Inns
A recent review
5 of 5 stars reviewed 5 weeks ago
Amy G Reading, Pennsylvania
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167 Reviews from our TripAdvisor Community

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
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There are newer reviews for Great Oak Manor
See the most recent reviews
Reading, Pennsylvania
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed 5 weeks ago

We were looking for a quiet place to spend some time away after a busy work season. My husband looked high and low and stumbled upon this place. The property is beautiful and wonderfully maintained. (inside and outside) The breakfasts, snacks and beverages were wonderful. We appreciated that we could bring our own things and that a fridge/freezer was supplied... More 

Was this review helpful? Yes 2
Delaware, Ohio
Level Contributor
5 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 26, 2015

This was a wonderful, clean, big B&B. I received a tour of the house. There were snacks in the afternoon with Sherry. There was a refrigerator stocked with quart size drinking water to take to your room. The rooms were large with large bathrooms. I had a fireplace in my room. The breakfasts were wonderful with more than enough to... More 

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Baltimore, Maryland
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 4, 2015

We stayed at Great Oak twice recently and could not have been happier. The grounds are fantastic, the rooms perfect and the whole inn such perfection. We were treated so beautifully, including tours of the inn, snacks and sherry in the afternoon, amazing breakfasts in the dining room and plenty of rooms to curl up and read or enjoy the... More 

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Amanda E, Assistant Innkeeper at Great Oak Manor, responded to this review

It was so nice to see you return so soon after your first visit! That means a lot to us and we are so glad to hear each stay was wonderful for you both. Now that I actually got that recipe to you, next time you're here you will have to tell me how the bread turned out! Looking forward... More 

washington, DC
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 14 helpful votes
5 of 5 stars Reviewed May 26, 2015

Beautiful property very convenient to Philly (and DC) and well maintained. Jen was great, flexible around our schedule and very accommodating. The location is great, with a beautiful yard pushing right up to the Bay. Made for a relaxing afternoon, and convenient to Rock Hall to head out on a sunset cruise (which Jen helped to line up!) We would... More 

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Mountain View, CA
Level Contributor
26 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 32 helpful votes
5 of 5 stars Reviewed May 24, 2015

While we weren't sure we were driving in the right direction, when we drove up the driveway what a pleasant scene came into view. Great Oak Manor! Amanda welcomed us, showed us to our rooms walked us through each public room and sat us on the back porch with a glass of champagne our daughters has ordered for Mother's Day.... More 

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Ocean City, New Jersey
Level Contributor
29 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed May 8, 2015

While we didn't spend too much time at the inn, our experience was peaceful and serene. The Marmaduke Room was tasteful and spacious with three windows overlooking the immaculately kept grounds. Breakfast was nicely presented. Day two, the dining room was crowded and lively, so we moved to the quieter Great Room and felt blessed to see a bald eagle... More 

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Level Contributor
3 reviews
5 of 5 stars Reviewed May 4, 2015

Just spent 2 days at the Manor. It is so much more than what the website shows. Everything about it is amazing, The most accommodating staff ever. We will return and I am telling everyone I know about it.

Was this review helpful? Yes
Jennifer D, Manager at Great Oak Manor, responded to this review

I'm so glad to hear you had a wonderful stay at Great Oak Manor. We appreciate you telling everyone about your recent discovery and stay, so thank you for that! It makes our day to hear from guests and even more so when they talk of how they fell in love with the place as much as everyone who works... More 

Delaware
Level Contributor
4 reviews
5 of 5 stars Reviewed April 12, 2015

Great Oak Manor has incredible views of the Chesapeake Bay. There's access to a small beach, which our dog loved! (No extra fee for bringing her! 2 dog-friendly rooms available) The manor is charmingly decorated with comfortable arm chairs and couches, the breakfast was great, and the rooms well appointed. We stayed Friday and Saturday, off-season, so the rates were... More 

Was this review helpful? Yes
Level Contributor
58 reviews
common_n_hotel_reviews_1bd8 39 helpful votes
4 of 5 stars Reviewed February 28, 2015 via mobile

We arrived to find to our surprise that our visit coincided with the first day under new ownership. Jenn, the inn manager that others have raved about, remains the innkeeper and was unfailingly helpful and cheerful. The house is nicely located with a beautiful view of the bay, and the sunset each evening over the water. There are several communal... More 

Was this review helpful? Yes 2
Jennifer D, Manager at Great Oak Manor, responded to this review

We're glad you enjoyed your time at Great Oak Manor and that you also got to share your visit with the new owners' first weekend! You really made the weekend special by being their first official guests. It was a pleasure meeting you both and we hope you return to see all of the new improvements that we have already... More 

Wallingford, Pennsylvania
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed January 17, 2015

My favorite place in the world to paint and watch birds. Amazing staff, best breakfast I've ever had at a B&B worldwide. Best view. Can't say enough nice things about the character of the building, furniture, library and did I mention VIEW! Eagles, kingfishers, herons, warblers, turkeys, etc. Binoculars provided! Can't say enough nice things about the Inn, Innkeeper, staff,... More 

Was this review helpful? Yes 1
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