Great Oak Manor

Property class: 3.5
Chestertown beachfront B&B with restaurant

Choose dates to view prices

Great Oak Manor offers a great location, putting you within just a 10-minute walk of Chesapeake Bay. Guests indulge in spa services, then grab a bite to eat at the restaurant. A fitness center, a snack bar/deli, and a terrace are other highlights.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Free breakfast
  • Spa
  • Free parking
  • Free WiFi
  • Restaurant
  • Air conditioning

Main amenities (12)

  • Daily housekeeping
  • On a private beach
  • Restaurant
  • WiFi in the lobby
  • Internet in the lobby
  • Fitness center
  • Spa services
  • 2 meeting rooms
  • Terrace
  • Coffee/tea in a common area
  • Air conditioning
  • Garden

Feel at home (6)

  • Rollaway/extra beds
  • Private bathroom
  • Premium TV channels
  • Garden
  • Terrace
  • Daily housekeeping

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The price is CNY724
CNY828 total
includes taxes & fees
Oct 11 - Oct 12
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About the neighborhood

Map
10568 Cliff Rd, Chestertown, MD, 21620

What's nearby

  • Washington College - 19 min drive - 18.0 km
  • River Arts Chestertown - 20 min drive - 19.4 km
  • Chestertown Historic District - 20 min drive - 19.7 km
  • Queenstown Premium Outlets - 56 min drive - 65.2 km
  • Queenstown Harbor Golf - 57 min drive - 66.2 km

Getting around

  • Baltimore Washington Intl. Airport (BWI) - 120 min drive
  • Baltimore, MD (MTN-Martin State) - 132 min drive

Restaurants

  • ‪Jellyfish Joel's - ‬16 min walk
  • ‪Mangroves Restaurant - ‬16 min walk
  • ‪The View at Worton Creek - ‬10 min drive
  • ‪O'Brien Compound Maryland Edition - ‬25 min drive
  • ‪Chestertown Cooking Company - ‬27 min drive

About this property

Great Oak Manor

  • Great Oak Manor offers a great location, putting you within just a 10-minute walk of Chesapeake Bay. Guests indulge in spa services, then grab a bite to eat at the restaurant. A fitness center, a snack bar/deli, and a terrace are other highlights.

At a glance

Hotel size

    • 12 rooms

Arriving/Leaving

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

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 21

Children

    • No cribs (infant beds)

Pets

    • Pets not allowed
    • Service animals welcome

Internet

    • WiFi and wired internet access in public areas*
    • Free WiFi in rooms

Parking

    • Free onsite self parking
    • Electric vehicle charging point on site

Other information

    • Smoke-free property

Property amenities

Food and drink

  • Free full breakfast each morning 9 AM–10 AM
  • Restaurant
  • Coffee/tea in a common area
  • Barbecue grills
  • Snack bar/deli

What to do

  • On a private beach
  • Kayaking
  • Canoeing
  • Free use of nearby fitness center

Working away

  • 2 meeting rooms

Services

  • Front desk (limited hours)
  • Concierge services
  • Tour/ticket assistance
  • Laundry facilities
  • Luggage storage
  • Bicycle rentals

Facilities

  • Safe-deposit box at front desk
  • Garden
  • Picnic area
  • Terrace
  • Library
  • Fitness center
  • Adjacent to a golf course
  • Spa services
  • Banquet hall

Accessibility

  • Wheelchair-accessible path of travel

Room amenities

Be entertained

  • Flat-screen television
  • Premium cable channels

Home comfort

  • Air conditioning
  • Bathrobes
  • Iron/ironing board

Sleep well

  • Premium bedding
  • Rollaway/extra bed (surcharge)

What to enjoy

  • Individually furnished and decorated

Freshen up

  • Private bathroom
  • Shower/tub combination
  • Free toiletries
  • Hair dryer
  • Towels

Stay connected

  • Desk
  • Free WiFi

Food and drink

  • Free bottled water

More

  • Daily housekeeping
  • In-room safe

Special features

Spa

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

Fees & policies

Optional extras

  • WiFi is available in public areas for an extra charge
  • Wired internet access is available in public areas for an extra charge

Children & extra beds

  • Rollaway beds are available for USD 35.0 per day

Pets

  • Service animals exempt from fees

Policies

Extra-person charges may apply and vary depending on property policy.
This property accepts credit cards.
Credit cards accepted: Visa, Mastercard, American Express, Discover

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

Are pets allowed at Great Oak Manor?

Sorry, pets aren't allowed, but service animals are welcome.

Is parking offered on site at Great Oak Manor?

Yes, there's free self parking. Electric vehicle charging is available.

What are the check-in and check-out times at Great Oak Manor?

Check-in start time: 3:00 PM; Check-in end time: 7:00 PM. Check-out time is 11 AM.

What is there to do at Great Oak Manor and nearby?

Have fun with onsite activities like kayaking, rowing, and cycling. Enjoy amenities like a private beach, a fitness center, and spa services. Great Oak Manor also has a picnic area and a garden.

Are there restaurants at or near Great Oak Manor?

Yes, there's an onsite restaurant.

What's the area around Great Oak Manor like?

Great Oak Manor is a short 5-minute walk from Chesapeake Bay and 5 minutes' walk from Northern Chesapeake Bay.

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Reviews

Great Oak Manor Reviews

9.6

Exceptional

9.8

Cleanliness

8.8

Location

9.8

Staff & service

9.4

Property conditions & facilities

Reviews

Verified review

6/10 Good

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 review

10/10 Exceptional

Plenty of privacy
Verified review

10/10 Exceptional

Great
Verified review

10/10 Exceptional

Always a quiet get away. People are friendly and welcoming.
Verified review

10/10 Exceptional

Very accommodating, quite, peaceful, very relaxing Just what we needed. Planning our next visit Highly Recomended Richard and Kathleen
Verified review

10/10 Exceptional

Beautiful location, friendly staff, clean and the beds were so comfortable!
Verified review

10/10 Exceptional

I liked the whole experience had at Great Oak Manor.
Verified review

10/10 Exceptional

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.
Verified review

8/10 Very good

Absolutely gorgeous setting and grounds. Breakfast was yummy and healthy. Lots of alternatives to eat. Gravel road driveway a little difficult to maneuver bags.
Verified review

10/10 Exceptional

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.
Verified review

10/10 Exceptional

Beautiful house and the grounds are amazing, we loved sitting on the beach watching the sunset. The property is waterfront.
Verified review

10/10 Exceptional

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.
Verified review

10/10 Exceptional

Perfect little getaway!
Verified review

8/10 Very good

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.
Verified review

10/10 Exceptional

The view and the amenities made it worth the stay
Verified review

8/10 Very good

Charm, sophistication, friendly atmosphere, and kind staff Could have longer reach on WiFi coverage - extending to chairs overlooking bay bluff.
Verified review

10/10 Exceptional

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.
Verified review

10/10 Exceptional

Great, friendly staff; building and grounds were excellently-maintained, room was comfy.
Verified review

10/10 Exceptional

Quaint, charming. Great place to relax and unwind.
Verified review

10/10 Exceptional

The location was spectacular! With a tweak or two, some of the baths need a little updating.
Verified review

8/10 Very good

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.
Verified review

10/10 Exceptional

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!!!
Verified review

10/10 Exceptional

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.
Verified review

10/10 Exceptional

We loved this place!

Great Oak Manor is beautiful, perfect place for a relaxing getaway weekend!
Verified review

10/10 Exceptional

Great Stay

Great stay.