We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

“We saw Elvis!” 5 of 5 stars
Review of Great Oak Manor Inn

We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In mm/dd/yyyy Check Out mm/dd/yyyy
Great Oak Manor Inn
Save Saved
You added Great Oak Manor Inn to your Saves list
10568 Cliff Rd, Chestertown, MD 21620   |  
Hotel amenities
Ranked #5 of 12 Chestertown B&B and Inns
Philadelphia, Pennsylvania
Senior Contributor
49 reviews 49 reviews
13 hotel reviews
Reviews in 16 cities Reviews in 16 cities
20 helpful votes 20 helpful votes
“We saw Elvis!”
5 of 5 stars Reviewed August 30, 2013

Ok, not really, but seeing 4 bald eagles on the estate at Great Oak Manor was just as exciting for us! My husband chose this spot for us, needing a getaway. Long ago, he yacht sat for some older friends at the marina there and would go up to the Manor's hammocks to read and relax on land. They were very gracious letting him lounge there during the week when there were few visitors. He never went in the house.

It is a stunning example of Georgian architecture! The service is wonderful, friendly and prompt. I will warn you though, that the pillows are rock-hard -- but Lisa did scavenge 2 fluffy ones for me so my 2nd night's sleep was divine. The breakfast is wonderful.

The 'lap poop' wasn't working which was ok -- it's one of those high powered small 'pools' where you swim against the current. Would be great if they replaced it with a large jacuzzi.

Exploring Chestertown was soooo much fun! There is something for all adults! In the Manor, we met a couple from North Jersey who were leaving a day early because 'there's not much to do around here!' First of all, who cares! The Manor is on stunning grounds, has a private beach and also beach/pool/golf/tennis access at the Marina which is next door, and exploring Kent County could have kept us engaged for several weeks!

History, great food, just enough nice boutiques. Try the crab soup at the Lemon Leaf cafe, shop at Mimi's boutique and the uber cute Twigs and Tea Cups. All the shop proprietress were so friendly and welcoming.

Do drive down to Great Neck Federal wildlife preserve, Rock Hall, and explore, explore, explore.

Room Tip: Ask for a water view. Do be aware that there are rooms on the 3rd floor so if you have trouble with...
See more room tips
  • Stayed August 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

142 reviews from our community

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
  • English first
  • Any
English first
Hemel Hempstead, England, United Kingdom
Reviewer
4 reviews 4 reviews
4 hotel reviews
Reviews in 4 cities Reviews in 4 cities
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed July 24, 2013

After driving for 6 hours from NYC and arriving late at night we were greeted by a very friendly lady. We were meant to stay in a different suite but they were having troubles with the shower so she gave us a free upgrade. The manor was stunning and peaceful she gave us a small tour and told us we could come down a bit later for breakfast as we had had a long journey. When entering the suite we couldn't believe our luck it was like we were in our own house it was huge! My mum and sister had the master bedroom which they both said was the most indulgent sleep they have ever had! I slept in the other room which was just as comfy. The bathroom was huge, lots of towels and very clean. The next morning we came down for breakfast which was beautifully served and the inn keeper was exceptional in making our stay memorable. It was so good we booked another night! Would definitely recommend this Inn to anyone visiting Chestertown.

  • Stayed July 2013, traveled with family
    • 4 of 5 stars Value
    • 4 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Doylestown, Pennsylvania
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed July 8, 2013

We had a large family gathering for a 4 day weekend...The Inn is Gorgeous! The Food was Fantastic! The Staff is WONDERFUL!!!
Jennifer the Inn Keeper is so accomodating and the rest of the crew made us feel like we were at home!!
We can't wait to go again!!!!

  • Stayed June 2013, traveled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Westminster, Maryland
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed April 20, 2013

I've been visiting Great Oak Manor since mid-1990's. Just returned from 4-day stay. As usual, it was difficult to leave the manor and everything it offers. If you're seeking a gorgeous view of the Bay, along with some peace, tranquility and exceptional comfort, this is the place for you. Great Oak is a true gem of Maryland's Eastern Shore. A++++++++!

  • Stayed April 2013, traveled solo
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewer
5 reviews 5 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed April 11, 2013

We stayed at the Great Oak Manor over a weekend to celebrate our wedding anniversary. It's gloriously situated right on the bay with a breathtaking sunset view which can be enjoyed from the glassed in conservatory on a chilly night or sitting in several romantically positioned adirondack chairs on the lawn. The manor is well decorated in the Georgian revival style as are the rooms. Guests are welcome to use the fireplaces in the common areas with the logs provided and some rooms also have fireplaces. We had two breakfasts and the first was to order as there were few other guests but the second day a lovely self serve buffet was laid out and the innkeeper was observant enough to provide us with a separate order of turkey bacon as we could not partake of the sausages. Overall our experience at this inn is was lovely. The bathroom in our room can probably use some updates but everything worked and the water pressure was good. The grounds are very well maintained and make for a good stroll if the weather cooperates. We'd love to come back here again.

  • Stayed March 2013
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Greenwich, Connecticut
Senior Contributor
31 reviews 31 reviews
11 hotel reviews
Reviews in 19 cities Reviews in 19 cities
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed October 9, 2012

My wife and I are frequent inn lodgers yet Great Oak was especially impressive with a handsome exterior and exquisite interior replete with old-school architectural details.

The property is lovely and the breakfast was terrific! The manager took the trouble to introduce herself and the staff was very accomodating.

The whole inn reminded us of our favorite B&B on a grander scale: Sweetwater Farm in Glen Mills, PA.

We are looking forward to our next trip and I'm thinking of trailing my boat down there for some spring bass fishing (out of the marina next door).

Room Tip: the inn is on the western side of Maryland's "eastern shore" so rooms on the back of...
See more room tips
  • Stayed September 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Annapolis, Maryland
Senior Contributor
33 reviews 33 reviews
12 hotel reviews
Reviews in 17 cities Reviews in 17 cities
28 helpful votes 28 helpful votes
5 of 5 stars Reviewed September 4, 2012

My husband and I live in the Baltimore/Annapolis area and can't believe we have never discovered this wonderful place! We went by boat on Labor Day weekend and had no idea what to expect. Hundreds of boats were in the cove, tied up and enjoying the fun of Jellyfish Joels, the tiki bar on the beach. Band playing, drinks flowing and an enormous mix of people. Young, old, families, singles. Something for everyone at this place. Tiki bar, playgrounds, golf, boats, pool, tennis, nice restaurants with awesome staff!

We were lucky enough to land a boat slip on one of the piers even though we didn't have reservations. The staff were very accomodating and the yearly slip-holders that were around us could not have been more friendly. A HUGE shout out to Pier C for making us feel welcome. We used the pool, which has a nice outside bar area. We had dinner at the restaurant, Mangroves, which had a nice mix of local favorite dishes as well as the tried and true.

If you're a boater, the bath houses were very clean and convenient from any pier. They also have adapters for electric if you don't have the correct one needed for shore power. Water and cable are also included in the slip cost as well as all of the other amenities on the property. There are even golf carts that will pick you up and take you to and from the tiki bar beach. If you opt to tie up in the cove, there is a free water taxi (though tips are greatly appreciated) that will pick you up and take you to the tiki bar or restaurant.

A gem of a place and definitely a place we would go again by car or water.

  • Stayed September 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Hotels you might also like...
mm/dd/yyyy mm/dd/yyyy
Price Your Stay

Been to Great Oak Manor Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Great Oak Manor Inn

Address: 10568 Cliff Rd, Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Amenities:
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( Wi-Fi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites Swimming Pool
Hotel Style:
Ranked #5 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $$
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 
Also Known As:
Great Oak Manor Hotel Chestertown

Owners: What's your side of the story?

If you own or manage Great Oak Manor Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.