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“The absolute best wedding, vacation spot on the east coast”
Review of Great Oak Manor

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Great Oak Manor
Ranked #2 of 11 Chestertown B&B and Inns
Certificate of Excellence
GreenLeadersGold level
Reviewed June 1, 2009

Our family stayed for one week and celebrated our daughter's wedding there. It was just perfect. We have gotten so many compliments from our guests saying it was the best wedding ever - we certainly believe so.

Our hosts John & Cassandra and their staff could not do enough for us - make sure you ask for Charlie. The rooms are all different and each one is prettier than the next. The entire manor is so inviting and comfortable. Don't miss this Oasis - go to fish, golf, shop, spend romantic time together and relax. We are already planning a family reunion. It is a perfect retreat and we just loved it! Stunning!!

  • Stayed: May 2009
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Thank luckylady39
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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341 - 347 of 386 reviews

Reviewed May 27, 2009

I was very impressed with my overall experience at the Great Oak Manor. The house is absolutely beautiful, the grounds are breathtaking and the owners Cassandra and John are most hospitable. The staff is warm, friendly and accommodating as well. We were at the Great Oak Manor for my cousins wedding and took over the Inn with family and friends. We had a great time, and felt very welcomed and at home. They do a fantastic job, not to mention how impeccable they keep the Inn, inside and out. I would highy recommend being a guest.

  • Stayed: May 2009, traveled with family
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Thank doglover1971
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 10, 2009

We arrived at this charming and secluded bed and breakfast inn on the first of three consecutive rainy days. On our first morning, we asked the owner what he'd recommend we do on a rainy day. "Stay here!" he said with enthusiasm. "It's a manor house and you don't get to stay in a place like this very often, so enjoy it." And he was right. There are a variety of spacious rooms beautifully furnished for a guest's comfort -- living rooms, a music room, a library, a conservatory, even an indoor pool in which one can relax and feel the stress ebbing away. The Chestertown area is rich with history and architectural attractions and Chesapeake Bay is a constant presence, but one can remain on the handsome grounds of the Great Oak Manor Inn for several days and not regret a second of it.

  • Stayed: May 2009, traveled as a couple
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Thank Teversall
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed April 12, 2009

My wife and I aren't usually impressed by luxury and pampering, but this vacation was one of those times where we really needed some down time and a nice place to spend it. The Great Oak Manor really delivered on all counts for us. We reserved The Tilden Room which is on the second floor with an awesome view of the expansive back lawn and the Chesapeake Bay. The room is very good size, with a comfortable king size bed. It was clean and attractive, and all of the little details were taken care of--interesting magazines to read, coasters for your drink, complementary Perrier. About the only downside was a small TV that received only over the air channels (or DVD's), and a small but well appointed bath.

The hosts, Cassandra and John went out of their way to make us feel at home. They knew our names, and spoke to us every day, usually several times to make sure we had appropriate recommendations for places to go and restaurants, etc. They had just the right balance of cheerful helping and letting us chill when we needed to.

The two highlights of our trip came on the last day. While looking out of our window, we saw two bald eagles in the trees, one carrying a freshly caught fish in his talons. The birds were just a few yards from our window, and we watched for almost 30 minutes. On Saturday evening, Casandra and John hosted a "special dinner" (they do this 8 times a year) which began with a wonderful classical and jazz pianist playing for 90 minutes in the music room, and then moved on to a 5 course meal prepared by John that was marvelous. Each course was very tasty and accompanied by its own wine selection. John even prepared a couple of special dishes to meet our special dietary needs. It was truly a feast!

This location doesn't offer the wide range of "resort" activities (no golf course, spa or tennis courts on site), but if you are after a quiet, pampered vacation stay, I would strongly recommend The Great Oak Manor!

  • Stayed: April 2009, traveled on business
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Thank DanaWins
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed April 6, 2009

I won a trip to the Great Oak Manor at my Hotels annual Christmas party several years ago. I have to admit I have never stayed at a bed and breakfast before, but I have toured through many of them. I work at a luxury hotel which is typically reffered to as an oversized B&B, but the Great Oak Manor is indeed a genuine bed & breakfast. The grounds of the Great Oak Manor are immaculate. It gives you a presidential feeling, a real sense of being back in colonial times...but in luxury! After hearing all the wonderful stories about the history of the place, its no wonder it gives you this feeling. There are many quiet areas throughout the building, as well as outside along the Chesapeake. John and Cassandra really make you feel at home. They are very inviting and friendly. After hearing their story about how they got involved with the Great Oak, it was plain to see that these two are very happy and comfortable with what they are doing there. They gave us great restaurant reccomendations, and the "Blue Heron" was excellent by the way! If you are looking for an A+ B&B experience, or a fabulous place to get married or engaged, please call John and Cassandra and let them make your dreams come true.

Cole Willey

  • Stayed: January 2006, traveled as a couple
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Thank NeverAHilton
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed March 25, 2009

John and Cassandra are the consumate hosts. They and their staff will see that you have a very enjoyable experience at the Manor. I have stayed there multiple times and am never disappointed in the accomodations, food, or service. The rooms are comfortable and spacious. The view of the River/Bay is beautiful and the grounds very relaxing. An ideal place to "get away from it all".

  • Stayed: March 2009, traveled with friends
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Thank Cruisergal54
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed March 25, 2009

You get a combination of the old fashioned feel of the 30's and touches of modern day. The staff is very professional, beds are comfortable and the grounds are beautiful. I love the staircase, each sitting room and little, clean beach with the beautiful white driftwood!

Will definately stay again!

  • Stayed: March 2009
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Thank 13oceanlover
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about Great Oak Manor

Address: 10568 Cliff Rd, Chestertown, MD 21620-4115
Phone Number:
Location: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites
Hotel Style:
Ranked #2 of 11 B&Bs / Inns in Chestertown
Price Range: $165 - $310 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 13
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 
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Also Known As:
Great Oak Manor Hotel Chestertown

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