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Traveller (183)
Room & Suite (64)
Storyboard
Overview
  • Excellent90%
  • Very good7%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“chesapeake bay”(77 reviews)
“private beach”(12 reviews)
“view of the bay”(11 reviews)
AMENITIES
Free Wifi
Free Parking
Breakfast included
Air Conditioning
Beachfront
Non-Smoking Hotel
Suites
3 Star accommodation
All hotel details
Additional information
Offers from Great Oak Manor
Special Offer: ☀️Summer Midweek Special
Offers from Great Oak Manor
Special Offer: ☀️Summer Midweek Special
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Rooms
26 Aug27 Aug
|
1 room, 2 adults, 0 children
Standard Room
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Reviews (400)
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400 results
Traveller rating
350
31
7
5
7
Traveller type
Time of year
LanguageEnglish
350
31
7
5
7
Show reviews that mention
All reviewschesapeake bayprivate beachview of the bayadirondack chairsbreathtaking viewsget awayeastern shorebald eaglesmy husband and ibreakfast was deliciousfrench toastsun roomrock hallwatching the sunsetbeautiful propertybed and breakfastfresh fruit
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1 - 5 of 400 reviews
Reviewed 1 week ago

The Great Oak Manor is absolutely beautiful. The setting is along the Chesapeake Bay on several acres of land. The landscape is beautiful and the Manor is a step back in time. The room (The Tylden) was comfortable and had a view of the harbor....More

Thank Cindy E
Response from General M, Manager at Great Oak ManorResponded 2 days ago

Thanks Cindy. We are always glad to hear that guests had a wonderful stay. It was our treat to meet you both and look forward to your next visit, which is soon, I hope.

Innkeeper's Favourite Review
Reviewed 5 March 2018 via mobile

Great Oak Manor is a splendid B&B When entering the property, you will be impressed by the shear grandness of the Inn’s massive size. Once inside, the attention to architectural detail and tasteful decor is quite impressive. My husband, who is a builder of fine...More

Thank heathpaul
Response from General M, Manager at Great Oak ManorResponded 6 March 2018

We so appreciate all of our guests and their kind remarks. I love the detail of this review as it speaks to everything about the Manor. Thank you for your kind words. We strive to make everyone's visit memorable and we look forward to having...More

Reviewed 3 weeks ago

This is the place to relax! Holly, Richard and Cass are truly welcoming people who make you feel totally at home right away. What a difference to be around people who clearly love what they do. Not much else to say - all amenities are...More

Thank snamor01
Response from General M, Manager at Great Oak ManorResponded 3 weeks ago

Thank you so much for your kind words. We appreciate knowing our guests had a Fantastic! experience. We hope to see you again.

Reviewed 3 weeks ago

This was our second stay at Great Oak Manor, the first being in a snowy February many years ago. The Manor has retained its beauty and charm. All rooms are beautifully decorated and its setting on the Chesapeake Bay is breathtaking. While taking a short...More

Thank mdpooh
Response from General M, Manager at Great Oak ManorResponded 2 days ago

Thank you for this wonderful review. We are so glad you found Great Oak Manor as delightful as you did on your first visit. Seeing our wonderful wildlife around here is a treat and I am so glad you were lucky enough to see the...More

Reviewed 4 weeks ago

My family enjoyed a second visit to the Great Oak Manor and we were thrilled with our rooms, scrumptious breakfast, and amazing grounds. Holly and Richard were so helpful and we were having so much fun that we decided at the last minute to add...More

Thank Maria G
View more reviews
About
Awards & Recognition
GreenLeaders Gold level
Certificate of Excellence
Amenities
Top amenities
Free Parking
Free High Speed Internet (WiFi)
Breakfast included
Beachfront
Hotel Amenities
Free Parking
Breakfast included
Pets Allowed ( Dog / Pet Friendly )
Banquet Room
Non-Smoking Hotel
Room amenities
Air Conditioning
Details
Price range
US$175 - US$394 (Based on Average Rates for a Standard Room)
Hotel class
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
Details
Price range
US$175 - US$394 (Based on Average Rates for a Standard Room)
Hotel class
Room types
Suites, Non-Smoking Rooms, Family Rooms, Accessible rooms
Add Photo Photos
Traveller (183)
Room & Suite (64)
Pool & Beach (14)
Dining (7)
Business Centre & Event Rooms (5)
Family and Play Areas (3)
Questions & Answers
Ask a question
Christopher G
4 October 2017|
AnswerShow all 6 answers
Response from General M | Property representative |
Chestertown does not shut down nor do the restaurants. It is a vibrant town with lots to do and with a rich history of colonial times and fishing the Chesapeake. There are wineries near by and even a wine trail for... More
0
Votes
Laurie A
7 April 2017|
AnswerShow all 4 answers
Response from GREATOAKMANOR | Property representative |
Nightly rates vary as to the type of room and whether it is weekday or weekend day. This month April they range from $149-$349 for weekday nights and $189-399 for weekends. There are currently some specials until the April... More
0
Votes
LKenney07
21 October 2015|
AnswerShow all 2 answers
Response from mileyjackie | Reviewed this property |
Yes. I was with an all women's bicycle touring group in which some of the women were gay. They come back every year to this wonderful B&B. They are very nice. Both the employees of the establishment and the bicycle group... More
1
Vote
Room Tips
"The Tylden has a view of the bay with a small balcony."
Read review
"Roese Room is lovely and great for a family; Sterling Room is ground floor and is also good for a family."
Read review
"3rd floor rooms are smaller, more affordable, and generally have better views than the lower floors. Worth..."
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"If the Carriage House is available, I'd book it!"
Read review
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