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Great Oak Manor

3.5 star property
3.5-star beachfront B&B near Chesapeake Bay

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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

On the beach.Within a 10-minute walk of the B&B, you'll find Chesapeake Bay and Northern Chesapeake Bay. Also within 9 miles (15 km) are Washington College and Larrabee Arts Center.
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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

3.5-star beachfront B&B near Chesapeake Bay
Simply step outside to unwind on the bed & breakfast's beach. Summer fun is a breeze at Great Oak Manor with activities like kayaking and rowing/canoeing.

Free breakfast is available daily. Along with a restaurant, there's a snack bar/deli on site. WiFi and wired Internet are available in public spaces for a fee. This beach bed & breakfast also offers a fitness center, a garden, and a terrace. Self parking is free.

This 3.5-star Chestertown bed & breakfast is smoke free.

  • 12 guestrooms or units
  • Full breakfast (free)
  • Deli
  • Charging station for electric cars
  • Coffee in lobby
  • Self-service laundry
  • Front desk (limited hours)
  • Storage area for luggage
  • Front-desk safe
  • Tour and ticket information
  • Concierge
  • Library
  • Terrace
  • Garden
  • BBQ grill(s)
  • Outdoor picnic space
  • No smoking on site
  • Dining venue
Great Oak Manor offers 12 air-conditioned accommodations with safes and complimentary bottled water. These individually decorated and furnished accommodations include desks. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include shower/tub combinations, bathrobes, complimentary toiletries, and hair dryers. This Chestertown bed & breakfast provides complimentary wireless Internet access. Housekeeping is provided daily.

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

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  • Parking included
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The price is $115
Jul 19 - Jul 20
Total with taxes and fees
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Property amenities

Family friendly

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

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

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

Room amenities

Entertainment

  • Flat-screen TV with premium cable channels

Bedroom

  • Premium bedding
  • Rollaway/extra bed (surcharge)

Bathroom

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

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

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are available for USD 35.0 per day.
  • Cribs (infant beds) are not available.

Property payment types

Important information

Optional extras

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

  • Rollaway bed fee: USD 35.0 per day

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

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property accepts Visa, Mastercard, American Express, and Discover.

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

How close is Great Oak Manor to the airport?

Great Oak Manor is 87.7 mi (132-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Great Oak Manor have an airport shuttle?

Airport shuttle services are not available at Great Oak Manor.

How close is Great Oak Manor to the beach?

This bed & breakfast is on a private beach. Don't forget your sunscreen!

Does Great Oak Manor offer free breakfast?

Great Oak Manor offers free full breakfast every day from 9 AM to 10 AM.

Is there a casino at Great Oak Manor?

No, there is no casino at this bed & breakfast.

What time is check-in at Great Oak Manor?

Check-in start time: 3:00 PM; Check-in end time: 7:00 PM.

Is there free parking at Great Oak Manor?

This bed & breakfast offers free self parking.

Does Great Oak Manor have a pool?

Great Oak Manor does not have a pool.

Does Great Oak Manor have a restaurant?

Yes, there is a restaurant on site.

Does Great Oak Manor have a spa?

This bed & breakfast doesn't have a spa, but it does offer spa services.

How close is Great Oak Manor to downtown Chestertown?

Great Oak Manor is 7.9 mi away from Chestertown.

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