Reviews

Score Breakdown based on 78 Reviews

4.5 out of 5
 
  • Guest room  4
  • Services  4
  • Value  4
  • Cleanliness  4
  • Dining  4

Explanation of Our Ratings

  Outstanding
  Exceeded my expectations
  Met my expectations
  Okay, but below average
  Unsatisfactory

Great stay ar Great Oak

About the reviewer

  • 55+ years old

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Gorgeous manor home in a serene setting

About the reviewer

  • 55+ years old

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A Great Get-Away

About the reviewer

  • 55+ years old

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Fabulous Place; Wonderful staff, food and views

About the reviewer

  • Between 45-55 years old

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A unique place

About the reviewer

  • 55+ years old

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Return to Great Oak

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Loved it! Owners really care!

About the reviewer

  • Between 36-45 years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A Perfect Weekend

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor was GREAT !

About the reviewer

  • 55+ years old

  • First time staying at a B&B

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Beautiful B&B

About the reviewer

  • Between 26-35 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Not Exactly in Chestertown, but Lovely

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Relaxing Getaway at Great Oak Manor

About the reviewer

  • Between 36-45 years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Favorite B&B

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Wonderful stay

About the reviewer

  • Between 18-25 years old

  • First time staying at a B&B

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

I can't wait to stay there again!

About the reviewer

  • Between 26-35 years old

  • Stays at B&Bs twice a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Stay

About the reviewer

  • Between 26-35 years old

  • First time staying at a B&B

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Birthday Celebration at Great Oak

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A peace of Heaven!

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

It does not get any better

About the reviewer

  • Between 18-25 years old

  • First time staying at a B&B

  • Typically stays in budget lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

our stay at Great Oak Manor

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Wonderful time at the Great Oak Manor

About the reviewer

  • 55+ years old

  • Almost never stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A Great Get-a-Way!

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in luxury lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

What a lovely estate. If you want to feel like you have stepped back in time to a gracious age of luxury, Great Oak Manor is for you. The grounds are lovely and the view is spectacular of the Chesapeake.

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great B&B by the Chesapeake

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Lovely Place - Highly Recommend It

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A little slice of heaven

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Real refinement

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

May weekend at Great Oak Manor

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs twice a year

  • Typically stays in budget lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Honeymoon

About the reviewer

  • Between 36-45 years old

  • First time staying at a B&B

  • Typically stays in moderate lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Loved our stay!!

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Wonderful, relaxing weekend

About the reviewer

  • Between 36-45 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A gem on the bay

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A little disappointing

About the reviewer

  • Between 36-45 years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Relaxing mid-winter escape

About the reviewer

  • Between 26-35 years old

  • Stays at B&Bs twice a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

excellent B & B experience

About the reviewer

  • 55+ years old

  • First time staying at a B&B

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

what a find!

About the reviewer

  • Between 45-55 years old

  • Almost never stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Quick Winter break at Great Oak Manor

About the reviewer

  • Between 45-55 years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Hidden Gem - afffordable, elegant, timeless and on waterfront!

About the reviewer

  • Between 45-55 years old

  • Almost never stays at B&Bs

  • Typically stays in budget lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Weekend in Chestertown

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor Stay

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling to visit family

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Very nice inn but not the best value for your money

About the reviewer

  • Between 26-35 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

If only we had more time...

About the reviewer

  • Between 26-35 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor-great bay location

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Wonderful place to stay

About the reviewer

  • Between 45-55 years old

  • Almost never stays at B&Bs

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A Delightful Weekend

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Romantic B&B for couples

About the reviewer

  • Between 26-35 years old

  • Stays at B&Bs twice a year

  • Typically stays in budget lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Beautiful Waterfront Estate

About the reviewer

  • Between 36-45 years old

  • Almost never stays at B&Bs

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Don't miss this experience

About the reviewer

  • Between 45-55 years old

  • Frequently stays at B&Bs

  • Typically stays in moderate lodging

  • Was travelling to visit family

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor is a delightful escape to another, quieter world

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

What a wonderful place!

About the reviewer

  • Between 45-55 years old

  • Frequently stays at B&Bs

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Excellent Getaway!

About the reviewer

  • Between 45-55 years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

The Best B&B

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Romantic Getaway in Sophisticated Yet Relaxed Atmosphere

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Repeat Experience....NEVER disappointed!

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A wonderful inn with wonderful innkeepers.

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in moderate lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor

About the reviewer

  • 55+ years old

  • First time staying at a B&B

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Magical Wedding at Breat Oak Manor

About the reviewer

  • Between 26-35 years old

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Escape

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

"C.H.A.O.S."

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Anniversary trip

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in luxury lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

elegant accomodations; super innkeepers

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in luxury lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

astounding

About the reviewer

  • Between 45-55 years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Pamper yourself - Visit Great Oak Manor

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs twice a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A Fabulous High Life Weekend at the Great Oak Manor

About the reviewer

  • Between 26-35 years old

  • First time staying at a B&B

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Memorial Day Weekend

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

My first time, will not be my last time

About the reviewer

  • Between 36-45 years old

  • First time staying at a B&B

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

What a relaxing retreat!

About the reviewer

  • Between 36-45 years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for an event

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A quiet, secluded retreat

About the reviewer

  • Between 45-55 years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Superior ambiance

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Oak Manor.

About the reviewer

  • Between 26-35 years old

  • Frequently stays at B&Bs

  • Typically stays in luxury lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

We'll go again

About the reviewer

  • 55+ years old

  • Frequently stays at B&Bs

  • Typically stays in premium lodging

  • Was travelling on vacation

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Great Place to Relax

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Beautiful and Relaxing

About the reviewer

  • Between 45-55 years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Annual Scrapbooking Weekend

About the reviewer

  • 55+ years old

  • Stays at B&Bs once a year

  • Typically stays in moderate lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Relaxing by the bay

About the reviewer

  • 55+ years old

  • Stays at B&Bs twice a year

  • Typically stays in premium lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

A perfect weekend getaway

About the reviewer

  • Between 36-45 years old

  • First time staying at a B&B

  • Typically stays in luxury lodging

  • Was travelling for a weekend getaway

  • Overall 
  • Guest Rooms 
  • Service 
  • Value 
  • Cleanliness 
  • Dining 

Quick Snap Shot


Explore Great Oak Manor

Check Availability Visit Website
  • Address 10568 Cliff Rd
    Chestertown, MD 21620-4115
    USA
  • Phone+1-410-778-5943
  • Toll free+1-800-504-3098
  • EmailContact Innkeeper