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.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

“Fabulous!”
5 of 5 bubbles Review of Great Oak Manor

Best prices for -
Check In dd/mm/yyyy Check Out dd/mm/yyyy
Prices are for 1 room, 2 adults
Show Prices
Compare best prices from top travel sites
and 6 more sites!
Great Oak Manor
Ranked #2 of 11 Chestertown B&B and Inns
Certificate of Excellence
GreenLeadersGold level
Chevy Chase MD
Level Contributor
10 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
“Fabulous!”
Reviewed 10 August 2011

This B&B has it all - beautiful rooms throughout, breathtaking views, and amazing food. The innkeepers, Cassandra and John are so gracious and made us feel so welcome. We enjoyed the beach and walking the grounds. It was totally relaxing. We are already looking forward to our next stay.
Catherine C.
Chevy Chase, MD

  • Stayed August 2011, travelled with friends
    • Value
    • Sleep Quality
    • Cleanliness
    • Service
Helpful?
Thank cecerecr
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Write a Review

341 reviews from our community

Traveller rating
    298
    26
    7
    4
    6
See reviews for
56
213
8
6
Rating summary
  • Location
    5 of 5 bubbles
  • Sleep Quality
    5 of 5 bubbles
  • Rooms
    4.5 of 5 bubbles
  • Service
    5 of 5 bubbles
  • Value
    4.5 of 5 bubbles
  • Cleanliness
    5 of 5 bubbles
Traveller tips help you choose the right room.   Room tips (72)
Date | Rating
  • English first
  • Any
English first
Washington DC, District of Columbia
Level Contributor
107 reviews
85 hotel reviews
common_n_hotel_reviews_1bd8 81 helpful votes
Reviewed 22 July 2011

This is a beautiful property with a great lawn that sweeps down to the bay. There is even a small beach for a swim in the bay on a hot summer day. Breakfasts are excellent as well with lots of variety - fruit, yogurt, muffins, something hot each day like french toast or omlettes. The center of Chestertown itself is 9 miles away and Rock Hall about 10 miles in a different direction. So you do have to be prepared to drive a bit for stores and restaurants but it's well worth it. The owner Cassandra is very nice, as is the dog. The property has been up for sale for a couple years but in this market, not much is moving and the owners maintain the place very well. We had one night where the air conditioning didn't work properly but they said they would have someone in to look at it as soon as they found out (It would't turn off .) We hope to go back for one of their off-season formal dinners. We took the only room with a balcony but no need. The balcony has a very high railing and you can't see very much. But our room was very nice and we saw another that was also beautiful.

  • Stayed July 2011, travelled as a couple
    • Value
    • Sleep Quality
    • Cleanliness
    • Service
Helpful?
Thank 4ontheroadMD
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Baltimore, Maryland
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
Reviewed 10 July 2011

M y husband and I recently returned from a mid-week stay at Great Oak Manor Inn where we had a wonderful time. Cordially welcomed by the staff, we were shown to our room, one of several in the Inn with a view of the Chesapeake Bay. Our room was spacious, very comfortable, and immaculate. On the walls of our room and throughout the Inn were attractive pieces of artwork. The breakfasts were excellent and included many choices, among which was delicious, seasonal fresh fruit. As I enjoy baking, I requested a few of the Inn's recipes, and the staff was happy to provide copies of them. After breakfast, we found no need for lunch, but in the afternoon the staff provided a fresh cake, fruit, cheese, and crackers, as well as delicious ice tea. And there were a lot of opportunities for fun. We took advantage of the chess set by the window on the second floor that overlooked the grounds, and the Inn provides bikes for those interested in riding through the countryside. After a staff member got us set up with bikes, she voluntarily supplied us with bottles of water to carry in our bike baskets, as she thought we might like them because the day was hot. After our ride, we used the lap pool in the conservatory and then went out to dry off on lawn chairs placed to overlook the Chesapeake Bay. We tried out the hammock, strung between two large shade-providing Black Walnut trees, while we watched the boats and ships go by, as well as various kinds of birds. The Inn is located in an area where there are many birds to see, and our room had a pair of binoculars, which we used. We had so much fun, and we definitely want to return because we had a truly remarkable experience.

  • Stayed July 2011, travelled as a couple
    • Value
    • Sleep Quality
    • Cleanliness
    • Service
Helpful?
1 Thank Nancyboydray
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Alexandria VA
Level Contributor
3 reviews
Reviewed 8 July 2011

We stayed 2 nights. Had front row seats for fireworks with the Bay as a backdrop. Cassandra and John were the most gracious hosts! Will definitely have a do over!

  • Stayed July 2011
    • Value
    • Location
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank JudgeBarbie
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Level Contributor
3 reviews
Reviewed 23 June 2011

Marvelously attentive Innkeepers and staff. They couldn't do enough to make us comfortable and feel like members of the family.

  • Stayed June 2011, travelled as a couple
    • Value
    • Sleep Quality
    • Cleanliness
    • Service
Helpful?
Thank PKA-Eagle
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Hotels you might also like...
Also consider these accommodations in or near Chestertown
12.3 km away
Holiday Inn Express Hotel & Suites Chestertown
12.4 km away
Quality Suites
Quality Suites
#2 of 2 in Chestertown
111 reviews
34.1 km away
The Inn at Chesapeake Bay Beach Club
Show Prices
Show Prices
Show Prices
35.3 km away
Waterfront Historic Kent Manor Inn
11.2 km away
Brampton Bed and Breakfast Inn
14.5 km away
The Inn at Osprey Point
The Inn at Osprey Point
#1 of 10 in Rock Hall
301 reviews
Show Prices
Show Prices
Show Prices

Been to Great Oak Manor? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Great Oak Manor

Property: Great Oak Manor
Address: 10568 Cliff Rd, Chestertown, MD 21620
Phone Number:
Region: 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 (per night): $251 - $433
Hotel Class:3.5 star — Great Oak Manor 3.5*
Number of rooms: 12
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 
Reservation Options:
TripAdvisor is proud to partner with Booking.com, Wotif.com, Expedia APAC, Hotels.com, Odigeo and lastminute.com.au so you can book your Great Oak Manor reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Also Known As:
Great Oak Manor Hotel Chestertown

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing