Great Oak Manor

Chestertown, Maryland

8.5

Select dates for prices

Check-in / Check-out

Show Prices

Jump to: Room choices | Hotel description | Map | Amenities | Reviews

Set your check-in and check-out dates in the form above to check availability.

About the Hotel

Step off the fast track to a place and time where the elegant living of yesteryear has been beautifully preserved. At Great Oak Manor in Chestertown, Maryland, the closest highway is the duck flyway and the only traffic you'll see from your charming Georgian-style guestroom are boats sailing on crystal waters. Within this magnificent country estate, recognized by American Historic Inns as among the Top Ten Most Romantic Inns, you'll luxuriate in that "get away from it all" feeling in a private and secluded locale on Chesapeake Bay.

Location

Great Oak Manor
10568 Cliff Rd.
Chestertown, Maryland 21620

Nearest Airport: MTN

Features and Amenities

Dining
Dining Room

In-Room Amenities
WiFi

Reviews for Great Oak Manor

BEAUTIFUL PLACE WITH KIND AND ATTENTIVE STAFF!!!

Reviewed 2 days ago

Wonderful weekend - "A Taste of Great Oak Manor"!! I attended this weekend event with family and enjoyed myself immensely!! The manor is warm and welcoming! The staff is friendly and attentive! Every room is inviting - the fire in the fireplaces, the chairs and the couches are comfortable, the selection of books in the library is fantastic! If you need a getaway or are looking for a place to hold a retreat, THE GREAT OAK MANOR IS YOUR PLACE!!! You will not be disappointed.

JCWill - New York

A Luxury Boutique Hotel That Feels Like Home

Reviewed 1 month ago

In the past couple years, I’ve been to Great Oak Manor several times, for work and pleasure. Holding a corporate meeting at the Manor allowed our team to gain a better understanding of each other and the business goals at hand. As a personal getaway, each visit to the Manor has left me feeling recharged and well nourished — the food is amazing! And last month, I hosted a guy’s retreat at the Manor for close friends over the past 20 years. It was a truly spiritual experience.

Parmanand S

Wonderful getaway!

Reviewed 2 months ago

This is a wonderful place for a getaway. The Great Oak Manor is a beautiful bed and breakfast. Superb food. Excellent service with attention to detail. Highly recommend this scenic, quiet, and luxurious space. I have been here several times- always exceeds my expectations!

Nadine S

If perfect was a place, Great Oak Manor would be it!

Reviewed 2 months ago

Great Oak Manor is a magical place. It certianly feels like a home away from home. I travel quite a bit and the beds at Great Oak Manor are some of the most comfortable I've ever slept in! The property is spotlessly clean and well decorated. The staff is kind, and attentive. The property is beautiful and serene - great for nature lovers. If perfect was a place, Great Oak Manor would be it!

Bernice M

Wonderful, Warm and Welcoming!

Reviewed 4 months ago

I stayed at Great Oak Manor as part of a women’s retreat program and it was such a wonderful experience. The property is located in a beautiful area of the Chesapeake with the most amazing sunsets. The property itself is also gorgeous - incredibly well maintained and decorated, with lots of elegant, luxurious but still comfortable details. Each room / suite is individually decorated with its own personality. The owners are wonderful, warm and welcoming hosts - it truly felt like a home away from home. The food was also extraordinarily delicious - the chef made meals to order, with fresh produce from the property and nearby farms. Even as a vegetarian, I was well-fed! I highly recommend a stay at Great Oak Manor - perfect for individual retreat or as part of a gathering of family and friends. I look forward to returning soon!!!

Companion48624