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.
All 12 Chestertown B&Bs / inns

Great Oak Manor Inn

10568 Cliff Rd, Chestertown, MD 21620
Hotel website
Hotel amenities
Great Oak Manor Inn
Ranked #4 of 12 Chestertown B&B and Inns
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
Write a Review

135 people have reviewed this hotel

Traveler rating
See reviews for
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 (11)
Date | Rating
  • English first
  • Any
English first
Washington DC, District of Columbia
3 reviews 3 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed November 15, 2013

We had three wonderful days at the inn. The room had a beautiful view of the Bay and the grounds were gorgeous and great for walking. On the day we left, we saw a pair of bald eagles. We stayed in the D'Oench room, and had a great bed. It felt too soft at first touch but we slept very... More

Was this review helpful? Yes
Philadelphia, Pennsylvania
Senior Contributor
46 reviews 46 reviews
10 hotel reviews
19 helpful votes 19 helpful votes
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... More

Was this review helpful? Yes
Hemel Hempstead, England, United Kingdom
4 reviews 4 reviews
4 hotel reviews
2 helpful votes 2 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... More

Was this review helpful? Yes
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!!!!

Was this review helpful? Yes 2
Westminster, Maryland
3 reviews 3 reviews
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++++++++!

Was this review helpful? Yes 1
3 reviews 3 reviews
1 helpful vote 1 helpful vote
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... More

Was this review helpful? Yes 1
Greenwich, Connecticut
17 reviews 17 reviews
7 hotel reviews
11 helpful votes 11 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... More

Was this review helpful? Yes 3
Annapolis, Maryland
Senior Contributor
29 reviews 29 reviews
10 hotel reviews
20 helpful votes 20 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... More

Was this review helpful? Yes
Savannah, GA
Senior Contributor
39 reviews 39 reviews
29 hotel reviews
20 helpful votes 20 helpful votes
4 of 5 stars Reviewed July 31, 2012

Great river views from room and expansive lawn in the back of a beautiful manor house. Spacious and comfortable room. Good staff...very accomodating. Ten minutes away from cute town with good restaurants. Would go back.

Was this review helpful? Yes 1
West Friendship, Maryland
2 reviews
5 of 5 stars Reviewed July 30, 2012

My husband and I stayed at the Inn for our 2 yr Anniversary. Jenn the Inn keeper made us feel right at home! When we got to our room we found a bottle of champagne with a little note telling us Happy Anniversary and enjoy our weekend. We took that bottle down to the water and enjoyed the views and... More

Was this review helpful? Yes

Been to Great Oak Manor Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Great Oak Manor Inn

Also Known As:
Great Oak Manor Hotel
Great Oak Manor Hotel Chestertown
Address: 10568 Cliff Rd, Chestertown, MD 21620
Phone Number:
Location: United States > Maryland > Chestertown
Bar / Lounge Beach Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Pets Allowed ( Dog / Pet Friendly ) Suites Swimming Pool
Hotel Style:
Ranked #4 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 

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.

Bookmark for later
Save Saved
You added Great Oak Manor Inn to your Saves list