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All 12 Chestertown B&Bs / inns

Great Oak Manor Inn

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10568 Cliff Rd, Chestertown, MD 21620
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Great Oak Manor Inn
Ranked #5 of 12 Chestertown B&B and Inns
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142 people have reviewed this hotel

Traveler rating
    125
    11
    4
    1
    1
See reviews for
11
85
5
4
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (13)
Date | Rating
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English first
There are newer reviews for Great Oak Manor Inn
See the most recent reviews
Queenstown, MD
Reviewer
3 reviews 3 reviews
3 hotel reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed November 25, 2007

Our Great Oak getaway was originally scheduled for early August. They say things happen for a reason, and in this case, I am so glad our plans had to change! We had a picture-perfect weekend - gorgeous fall colors, unique snow geese in a pond and fields on the road leading up to the manor house, and a bright sunny... More

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Fallbrook, CA
Reviewer
5 reviews 5 reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed November 13, 2007

My wife and I just spent two very relaxing and pleasant nights at Great Oak Manor. This is the first time we stayed at a B & B for quite some time and we both agreed we want to stay at Select Registry B & B's whenever we have an opportunity going forward. If you want to go to a... More

Was this review helpful? Yes 1
Virginia
2 reviews
5 of 5 stars Reviewed August 25, 2007

Beautiful, classy, tasteful, and quality are words that come to mind to describe the Great Oak Manor. We highly recommend it for a quiet getaway or a group event; we plan to return. We particularly liked the "extras" like great coffee, tea, soft drinks, fruit, ice & glasses available all day starting at 7 am. More snacks were supplied during... More

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Philadelphia
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 7, 2007

My husband and I have been to the Manor three times and have always had a wonderful time. We've stayed in different rooms and all are lovely. Innkeepers are wonderful - accomodating without being overly involved with the guests. It's obvious they enjoy their Inn and want you to relax and enjoy as well. We have two small children, so... More

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Virginia
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed May 10, 2007

Just like the Otis Redding song "Sitting by the Dock of the Bay", the Great Oak Manor has perfected the art of getting away by the bay. When asked by friends to find something wrong with our three-night stay all we could think of was that it was too short. The elegant accommodations, gracious hosts, friendly staff and delightful cats... More

Was this review helpful? Yes 1
Corte Madera, California
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 15, 2007

This B & B is my favorite place to go for our scrapbook escape weekends. Wonderful space to work with our group of 12 or more and the grounds are perfect for watching setting suns and long walks. Hosts treat us like their favorite child and serve the best breakfasts.We are pampered with all our requests, THE best place to... More

Was this review helpful? Yes 1
Atlanta
1 review
5 of 5 stars Reviewed January 16, 2007

Having booked our stay "sight unseen," we were thrilled with the first impression of the Great Oak Manor, and continued to be even more pleased as our visit continued. The innkeepers, Cassandra and John, are gracious, welcoming and knowledgeable about the surrounding area, directing us to restaurants, shops, events and other points of interest. Their interest in making our time-away-from-home... More

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Glenside, PA
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed January 13, 2007

It has been a week since our stay at Great Oak Manor B&B, and we are still savoring the experience. Superlatives come to mind about everything to do with Great Oak. It is the best B&B we have visited, and we expect to return. Great Oak is located on the Eastern Shore of the Chesapeake, overlooking the Bay. The Manor... More

Was this review helpful? Yes 1
Potomac Falls, Virginia
1 review
5 of 5 stars Reviewed January 2, 2007

We have stayed at Great Oak Manor 6 times this year (2006), and 12 times over the last 3 years, and we always find Great Oak to be a most relaxing and romantic experience. The owners of Great Oak ensure that our stay is always a memorable one, from the second we enter the Inn until we leave. The rooms... More

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alexandria, va
Reviewer
4 reviews 4 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed December 21, 2006

My husband and I stayed for a weekend, to getaway and relax. this waterfront inn was THE best place to relax, read, walk, dine and just spent precious time together. The innkeepers couldn't be more hospitable and at the same time, gave us privacy and peace and quite. The breakfast in the dining room was more than we could eat;... More

Was this review helpful? Yes 1
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Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Price Range (Based on Average Rates): $$
Also Known As:
Great Oak Manor Hotel Chestertown

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Amenities

Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites Swimming Pool
Official Description (provided by the hotel)
Great Oak Manor on the eastern shore of the Chesapeake Bay is aglow in 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 waterfront. With 11 guestrooms, Great Oak offers the finest in a romantic luxury bed and breakfast inn. ... more   less 
Number of rooms
11

Questions & Answers

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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?

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