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Great Oak Manor

3.5 star property

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Photo gallery for Great Oak Manor

Property grounds
Private beach, kayaking, rowing
Exterior
Deluxe Suite, 1 King Bed, Fireplace (Roese) | Premium bedding, in-room safe, individually decorated
Free daily full breakfast

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • On private beach
  • Breakfast included
  • Spa
  • Parking included
  • Free WiFi
  • Restaurant

Explore the area

View in a map
10568 Cliff Rd, Chestertown, MD, 21620
  • Place, Washington College
    ‪19 min drive‬
  • Place, River Arts Chestertown
    ‪20 min drive‬
  • Place, Chestertown Historic District
    ‪20 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪127 min drive‬

Room options

About the neighborhood

Chestertown

Great Oak Manor places you within a 10-minute stroll of Chesapeake Bay and Northern Chesapeake Bay. This 3.5-star bed & breakfast welcomes guests with 12 rooms and conveniences like a private beach, free in-room WiFi, and free self parking.
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What's nearby

  • Washington College - 19 min drive - 11.2 miles
  • River Arts Chestertown - 20 min drive - 12.0 miles
  • Chestertown Historic District - 20 min drive - 12.3 miles
  • Wilmer Park - 20 min drive - 12.3 miles
  • Historical Society of Kent County Maryland - 20 min drive - 12.3 miles

Getting around

  • Baltimore Washington Intl. Airport (BWI) - 120 min drive

Restaurants

  • ‪Jellyfish Joel's - ‬16 min walk
  • ‪Tolchester Marina Beach Bar - ‬24 min drive
  • ‪Mangroves Restaurant - ‬16 min walk
  • ‪JR's Watermark Grille - ‬16 min walk
  • ‪W A Clark Jr and Son - ‬7 min drive

About this property

Great Oak Manor

Guests staying at Great Oak Manor enjoy access to a private beach, a gym, and WiFi in public areas. You can put free parking to good use if you drive. Front-desk staff can assist with luggage storage, concierge services, and securing valuables. Other amenities at this beach bed & breakfast include coffee/tea in a common area, a library, and a terrace.
Flat-screen TVs come with cable channels, and free WiFi keeps guests connected. Beds are dressed in premium bedding and bathrooms offer hair dryers and free toiletries. Safes, ironing boards, and desks are also standard.
Recreational amenities at the bed & breakfast include a private beach and a fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guests can pamper themselves by indulging in the onsite spa services.

Similar properties

Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing
Chestertown
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
7.8 out of 10, Good, 88 reviews
$151 nightly
The price is $168
Jun 28 - Jun 29
Total with taxes and fees
The Lodge at Great Oak Landing

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: WiFi (surcharge); wired internet (surcharge)

Parking and transportation

  • Electric car charging station on site
  • Free self parking on site

Food and drink

  • Free full breakfast available daily 9:00 AM to 10:00 AM
  • A restaurant
  • Coffee and tea in common areas
  • Snack bar/deli

Things to do

  • 9-hole adjacent golf course
  • Bicycle rentals
  • Gym
  • Kayaking
  • Library
  • Rowing/canoeing

Family friendly

  • Laundry facilities
  • Rollaway/extra bed (surcharge)
  • Snack bar/deli

Conveniences

  • Laundry facilities
  • Limited-hour front desk
  • Luggage storage
  • Safe at front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Tour and ticket assistance

Business services

  • 2 meeting rooms

Outdoors

  • Barbecue grill
  • Garden
  • On a private beach
  • On the bay
  • Picnic area
  • Terrace

Spa

  • Spa services

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair-accessible path of travel

More

  • Banquet hall
  • Smoking not allowed

Room amenities

Bedroom

  • Premium bedding
  • Rollaway/extra bed (surcharge)

Bathroom

  • Bathrobes
  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower/bathtub combination
  • Towels provided

Entertainment

  • Flat-screen TV with premium cable channels

Food and drink

  • Free bottled water

More

  • Air conditioning
  • Desk
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Safe

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 7:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11 AM

Special check-in instructions

The front desk is open daily from 9 AM - 9 PM
Guests must contact the property in advance for check-in instructions; front desk staffed during limited hours
To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation
If you are planning to arrive after 7 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

  • Service animals exempt from fees

Children and extra beds

  • Rollaway/extra beds are available for USD 35.0 per day

Property payment types

Important information

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • Rollaway bed fee: USD 35.0 per day

This list may not be comprehensive. Fees and deposits might not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards
  • Check-in: 3:00 PM
  • Check-out: 11 AM
  • Minimum check-in age: 21
The front desk is available during limited hours. Driving? This property offers free parking, along with a car charging station.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards.

Additional information about polices, regulations, and more:

  • No cribs or infant beds are available.

Property is also known as

Great Oak Manor B&B Chestertown
Great Oak Manor B&B
Great Oak Manor Chestertown
Great Oak Manor
Great Oak Manor Hotel Chestertown
Great Oak Manor Chestertown
Great Oak Manor Bed & breakfast
Great Oak Manor Bed & breakfast Chestertown

Frequently asked questions

What's there to see near Great Oak Manor?

This bed & breakfast in Chestertown is within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay. You'll also find Kinnairds Point Drive and Pooles Island Light nearby.

Will I be able to park at Great Oak Manor?

Yes, self parking is offered for free at the bed & breakfast. An electric car charging station is also available for guests.

Does Great Oak Manor have a casino?

No, Great Oak Manor doesn't have a casino.

Will I find an indoor pool at Great Oak Manor?

No, there is no indoor pool at this bed & breakfast.

Is Great Oak Manor good for couples?

There are many amenities for couples at this bed & breakfast, including a private beach and a restaurant plus some guestrooms feature a fireplace.

Does Great Oak Manor have a hot tub?

No, this bed & breakfast doesn't have a spa tub.

Does Great Oak Manor have a restaurant that serves breakfast?

Yes, Great Oak Manor serves free full breakfasts each morning from its restaurant.

Will Great Oak Manor allow pets to stay for free?

No, pets aren't allowed at Great Oak Manor though service animals are welcome.

Does Great Oak Manor have connecting rooms available?

No, there aren't connecting guestrooms at this bed & breakfast.

What is the closest airport to Great Oak Manor?

The closest major airport to Great Oak Manor is Baltimore, MD (MTN-Martin State), which is about 12.5 mi away. Another top airport is Baltimore Washington Intl. Airport (BWI), which is around 25.8 mi away.

Can I book a room with a balcony at Great Oak Manor?

Yes, some guestrooms at this bed & breakfast offer a balcony where guests can enjoy ocean and garden views.

Great Oak Manor Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 34 out of 44 reviews
Rating 8 - Good. 8 out of 44 reviews
Rating 6 - Okay. 2 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.4/10

Amenities

9.4/10

Property conditions & facilities

Reviews

Verified

6/10 Okay

Scott

Liked: Cleanliness, staff & service, room comfort

Spotty stay

We had a nice stay but with a few areas lacking. This B and B is on the expensive side with beautiful grounds and an impressive entrance. Our third floor room was outdated and had a former that was too high to enjoy the view of the lawn and river. Breakfast was served from nine to ten. We arrived to the dining room at 9:20 and the buffet breakfast was in need of replenishment. We were told it's hard to keep things hot past 9:30. I asked if we were to arrive at nine but he said no anytime between 9 and 10 is fine. There were silver plated items on the built in shelves that were badly in need of polishing and most of the flowered in the small arrangements on each table were dead. The food was fairly good not great.
Verified

10/10 Excellent

Drew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Plenty of privacy
Stayed 2 nights in Feb 2022
Verified

10/10 Excellent

Blanca

Liked: Cleanliness, staff & service, property conditions & facilities
Great
Stayed 2 nights in Jan 2022
Verified

10/10 Excellent

Trina

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always a quiet get away. People are friendly and welcoming.
Stayed 1 night in Jan 2022
Verified

10/10 Excellent

Richard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very accommodating, quite, peaceful, very relaxing Just what we needed. Planning our next visit Highly Recomended Richard and Kathleen
Stayed 2 nights in Sep 2021
Verified

10/10 Excellent

Lynda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Beautiful location, friendly staff, clean and the beds were so comfortable!
Stayed 1 night in Aug 2021
Verified

10/10 Excellent

Verified traveler

Liked: Staff & service, amenities, property conditions & facilities
I liked the whole experience had at Great Oak Manor.
Stayed 2 nights in May 2021
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
What a charming property, it has such character. Super clean and well kept that you feel almost at home. The staff are fantastic and make sure that you have everything you need. Breakfast was fantastic and changed daily. I have dietary restrictions and they made a special omelette with no issue when I could not have the 2 main options. We stayed in the Marmaduke room and loved it. Each room has its own look and feel from what I could see. The main thing that really makes this nice is that no kids are allowed under 12. This makes it more of an adult getaway. Sit by the fire, go for a bike ride and drink some wine or by the water and enjoy some peace and quiet.
Stayed 2 nights in May 2021
Verified

8/10 Good

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities
Absolutely gorgeous setting and grounds. Breakfast was yummy and healthy. Lots of alternatives to eat. Gravel road driveway a little difficult to maneuver bags.
Stayed 1 night in Apr 2021
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful manor, well cared for. Friendly and attentive staff, even the other guests were friendly. High level of cleanliness. Breakfast was delicious. Loved that it was dog friendly. A number of activities available on site- fire pit, kayaking.
Stayed 1 night in Apr 2021
Verified

10/10 Excellent

Yvonne

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful house and the grounds are amazing, we loved sitting on the beach watching the sunset. The property is waterfront.
Stayed 1 night in Sep 2020
Verified

10/10 Excellent

DonO

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Inn was very nice and the caretakers, Joe & Holly, were friendly and hospitable. The Manor has a low key, homey vibe to it which was welcome as some Inn's can be very stuffy and pretentious. The architecture was neat and grounds appealing an well kept. Breakfasts were good and hearty. Our room (Henson) was nice but one wall was in need of repair (due to a leak?). It, along with some others, was on a 3rd floor and no elevator, so be sure to factor that in any reservations. The Manor is just minutes down the shore from a nicer beach and a Tiki Bar if you'd like something other than peace and quiet.
Stayed 2 nights in Aug 2020
Verified

10/10 Excellent

Kate

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Perfect little getaway!
Stayed 1 night in Aug 2020
Verified

8/10 Good

John

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great Oak visit

We enjoyed our stay. Upscale and lovely setting, very rural area. Quiet. Our balcony room was very nice but the Juliet balcony (picture) wasn't one to pay extra for. Broad expanse of greenery on the property, included breakfast just fine, convenient parking. The beach is "down the hill" - accessible with a pretty good walk. Room nice, bathroom small but adequate, shower knob was tricky as it rotated 360 degrees but only worked through 180. The TV system was Direct TV but with no channel guide, never did figure that one out.
Stayed 2 nights in Jul 2020
Verified

10/10 Excellent

Tammy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The view and the amenities made it worth the stay
Stayed 2 nights in Jun 2020
Verified

8/10 Good

Verified traveler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Charm, sophistication, friendly atmosphere, and kind staff Could have longer reach on WiFi coverage - extending to chairs overlooking bay bluff.
Stayed 3 nights in Jun 2020
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Memorial weekend 2020

Beatufil property in a beautiful location. Staff was super helpful and friendly. Breakfast was great and very well organized for social distancing. cleaning etc.
Stayed 2 nights in May 2020
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great, friendly staff; building and grounds were excellently-maintained, room was comfy.
Stayed 1 night in Dec 2019
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint, charming. Great place to relax and unwind.
Stayed 1 night in Dec 2019
Verified

10/10 Excellent

Bob

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The location was spectacular! With a tweak or two, some of the baths need a little updating.
Stayed 2 nights in Nov 2019
Verified

8/10 Good

Verified traveler

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed our stay here. The grounds are beautiful and it's right on the water. We enjoyed playing cornhole on the lawn, taking the kayaks out and having a fire on the banks of the water. Our bed was comfortable, the water was hot and breakfast was plentiful the few times we ate it and the staff was friendly and helpful. There are lots of nice common areas and our room and bathroom were huge. The inn is older and definitely has that musty, older smell. I'm not sure how you get rid of that, but it's really the only thing about the inn that I really didn't care for. I didn't realize that it was as far from Chestertown as it was, so we had to drive to get anywhere and to go eat, which wasn't what I had in mind when I booked it (but that's my fault). Also, there aren't many decent places to eat in Chestertown so that was a pretty big bummer too. But again, that has nothing to do with the inn itself. I wouldn't hesitate to stay here again, maybe in the summer when there is more to do/more places open, etc.
Stayed 3 nights in Oct 2019
Verified

10/10 Excellent

JannaD

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
If you are looking for a peaceful, relaxing and restful vacation, this is the place. Breakfasts are phenomenal!!! Holly is the exceptional host. Rooms are nice, clean and taken care of. I loved the history of the house. Great local restaurants. We had an amazing time!!!
Stayed 3 nights in Jul 2019
Verified

10/10 Excellent

Lucy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property is absolutely beautiful. It deserves more than five stars for elegance and relaxation. It couldn’t have any more amenities. We stayed for two nights and couldn’t get it all in! We will definitely go back.
Stayed 2 nights in Jun 2019
Verified

10/10 Excellent

Kirwan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

We loved this place!

Great Oak Manor is beautiful, perfect place for a relaxing getaway weekend!
Stayed 3 nights in May 2019
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great Stay

Great stay.
Stayed 1 night in Apr 2019