Guests
All properties in Chestertown, Maryland, United States of America

Great Oak Manor

Chestertown romantic B&B with private beach

  • Free full breakfast, free WiFi, and free parking
From
P10,093

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  • Great Oak Manor
  • Great Oak Manor
  • Beach
  • Deluxe Apartment, 2 Bedrooms, Bay View (Carriage House)​ - Living Room
  • Great Oak Manor
Great Oak Manor. Image 1 of 91.
1 / 91Great Oak Manor
10568 Cliff Rd, Chestertown, 21620, MD, United States of America
9.6.Exceptional.
  • Beautiful location, friendly staff, clean and the beds were so comfortable!

    Aug 22, 2021

  • I liked the whole experience had at Great Oak Manor.

    May 23, 2021

See all 33 reviews

Enhanced health and safety measures

This property advises that enhanced cleaning and guest safety measures are currently in place.
  • Property is cleaned with disinfectant
  • Staff wears personal protective equipment
  • Property confirms they are implementing enhanced cleaning measures
  • Guests are provided with free hand sanitizer

Guests rated location

Quiet
Safe
Easy parking
  • Free WiFi
  • Free parking
  • Bathtub
  • Non-smoking
  • Gym
  • Air Conditioning

Property highlights

Main amenities

  • 12 smoke-free guestrooms
  • Daily housekeeping
  • On a private beach
  • Fitness center
  • Spa services
  • Terrace

What’s around

  • On a private beach
  • Washington College - 9.1 mi / 14.6 km
  • Rock Hall Harbor - 12.6 mi / 20.2 km

Book this property and collect stamps after your stay

Remember, collect 10 stamps, get 1 reward* night

Enter dates for 2 guests

Guests
  • Premier Room, 1 King Bed, Fireplace, Bay View (Marmaduke)
  • Superior Room, 1 King Bed, Balcony, Bay View (Tylden)
  • Exclusive Room, 1 King Bed, Fireplace, Bay View (D'Oench)
  • Deluxe Room, 1 King Bed, Balcony, Bay View (Caulk)
  • Deluxe Room, 1 King Bed
  • Romantic Room, 1 King Bed, Fireplace (Wicks)
  • Premium Suite, 1 Bedroom, Accessible, Patio (Sterling)
  • Luxury Suite, 1 King Bed with Sofa bed, Fireplace, Bay View
  • Classic Room, Bay View (Geddes-Piper)
  • Deluxe Room, Bay View (Hynson)
  • Deluxe Room (Ringgold)
  • Deluxe Suite, 1 King Bed, Fireplace (Roese)
  • Deluxe Apartment, 2 Bedrooms, Bay View (Carriage House)​

What’s around

Landmarks

  • On a private beach
  • Washington College - 9.1 mi / 14.6 km
  • Rock Hall Harbor - 12.6 mi / 20.2 km

Getting around

  • Baltimore Washington International Airport (BWI) - 105 min drive
  • Baltimore, MD (MTN-Martin State) - 122 min drive
map
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10568 Cliff Rd, Chestertown, 21620, MD, United States of America

At a glance

Size

  • 12 rooms

Arriving/leaving

  • Check-in time 3:00 PM-7:00 PM
  • Check-out time is 11 AM

Restrictions related to your trip

  • Check COVID-19 restrictions.

Special check-in instructions

The front desk is open daily from 9 AM - 9 PM. If you are planning to arrive after 7 PM please contact the property in advance using the information on the booking confirmation. Front desk staff will greet guests on arrival.

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 allowed*
  • Specific rooms only, restrictions apply*

Internet

  • Free WiFi in public areas
  • Free WiFi in rooms

Parking

  • Free onsite self parking

Other information

  • Smoke-free property
*See fees & policies for additional details or extra charges

At the property

Food and drink

  • Free full breakfast daily
  • Snack bar/deli
  • Coffee/tea in a common area
  • Barbecue grills

Things to do

  • On private beach
  • Fitness facilities
  • Spa services on site
  • Bicycle rentals on site
  • Kayaking on site
  • Rowing or canoeing on site
  • Free use of nearby fitness center

Services

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

Facilities

  • Safe-deposit box at front desk
  • Garden
  • Picnic area
  • Terrace
  • Library

Accessibility

  • Accessible bathroom
  • In-room accessibility
  • Wheelchair-accessible path of travel

In the room

Home comforts

  • Air conditioning
  • Bathrobes
  • Iron/ironing board

Sleep well

  • Premium bedding

Things to enjoy

  • Individually decorated
  • Individually furnished

Freshen up

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

Be entertained

  • Flat-screen TV
  • Premium TV channels

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

Children & extra bedsPay at property

  • Rollaway beds are available for USD 35.0 per day

PetsPay at property

  • Pets are allowed for an extra charge of USD 25 per pet, per day
  • Contact the property at the number on the booking confirmation for details on pet restrictions and to request a pet-friendly room

Hygiene & cleanliness

This property advises that enhanced cleaning and guest safety measures are currently in place.

Disinfectant is used to clean the property, and commonly-touched surfaces are cleaned with disinfectant between stays.

Staff at the property wear personal protective equipment and guests are provided with hand sanitizer.

Policies

This property accepts Visa, Mastercard, American Express and 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

*See fees & policies for additional details or extra charges

FAQs

  • This property confirms that disinfectant is used to clean the property. Furthermore, guests are provided with hand sanitizer, and staff are given personal protective equipment. Please note that this information has been provided by our partners.
  • Yes, there's free self parking.
  • Yes, pets are welcome. There's a charge of USD 25 per pet, per day.
  • You can check in from 3:00 PM - 7:00 PM. Check-out time is 11 AM.
  • Have fun with onsite activities like kayaking and rowing. Enjoy amenities like a private beach, a fitness center, and spa services. Great Oak Manor also has a picnic area and a garden.
9.6.Exceptional.
  • 10.0.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.

    2 night family trip, May 7, 2021

    Verified Orbitz guest review

  • 8.0.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.

    1 night romance trip, Apr 10, 2021

    Verified Expedia guest review

  • 10.0.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.

    1 night romance trip, Apr 4, 2021

    Verified Expedia guest review

  • 10.0.Exceptional

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

    Yvonne, 1 night family trip, Sep 28, 2020

    Verified Expedia guest review

  • 10.0.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.

    DonO, 2 night romance trip, Aug 23, 2020

    Verified Expedia guest review

  • 10.0.Exceptional

    Perfect little getaway!

    Kate, 1 night trip, Aug 12, 2020

    Verified Hotels.com guest review

  • 8.0.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.

    John, 2 night trip, Jul 20, 2020

    Verified Hotels.com guest review

  • 10.0.Exceptional

    The view and the amenities made it worth the stay

    Tammy, 2 night romance trip, Jun 29, 2020

    Verified Expedia guest review

  • 8.0.Very good

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

    3 night family trip, Jun 2, 2020

    Verified Expedia guest review

  • 10.0.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.

    2 night trip, May 23, 2020

    Verified Hotels.com guest review

See all 33 reviews