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Great Oak Manor

3.5 star property
3.5-star beachfront B&B with free breakfast

Choose dates to view prices

Great Oak Manor

Photo gallery for Great Oak Manor

Property grounds
Property grounds
Deluxe Room, 1 King Bed, Balcony, Bay View (Caulk) | Premium bedding, in-room safe, individually decorated
Food and drink
View from room

Overview of Great Oak Manor

Reviews
9.4

Exceptional

Popular amenities

  • Breakfast includedBreakfast includedBreakfast included
  • On private beachOn private beachOn private beach
  • SpaSpaSpa
  • Parking includedParking includedParking included
  • Free WiFiFree WiFiFree WiFi
  • LaundryLaundryLaundry

Explore the area

Map
10568 Cliff Rd, Chestertown, MD, 21620
  • Popular LocationWashington College19 min drive
  • Popular LocationRiver Arts Chestertown20 min drive
  • AirportBaltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)105 min drive
  • Popular LocationBaltimore Inner Harbor Marina112 min drive

Room options

About the neighborhood

Chestertown

On the beach.You'll be within 9 miles (15 km) of Washington College and 16 miles (25 km) of Rock Hall Harbor. Betterton Beach is 14.2 mi (22.9 km) away.
View more B&B in ChestertownOpens in a new window

What's nearby

  • Washington College - 19 min drive
  • River Arts Chestertown - 20 min drive
  • Baltimore Cruise Terminal - 110 min drive
  • National Aquarium in Baltimore - 112 min drive
  • Baltimore Inner Harbor Marina - 112 min drive

Getting around

  • Baltimore Washington Intl. Airport (BWI) - 105 min drive

Restaurants

  • Jellyfish Joel's - 16 min walk
  • Mears Great - 16 min walk
  • Tolchester Restaurant - 24 min drive
  • Clark Seafood - 7 min drive
  • JR's Watermark Grille - 16 min walk

About this property

Great Oak Manor

3.5-star beachfront B&B with free breakfast
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. There's a snack bar/deli on site. WiFi is free in public spaces. 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
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.

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: Free WiFi

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–10:00 AM
  • Coffee and tea in common areas
  • Snack bar/deli

Things to do

  • 9 holes of golf
  • 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

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 staff will greet guests on arrival
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

Access methods

Staffed front desk

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 87.6 mi (122-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 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 0.3 mi away from Great Oak Landing.

Great Oak Manor Reviews

Reviews

9.4

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" "

9.6/10

Cleanliness

9.6/10

Staff & service

9.4/10

Amenities

9.4/10

Property conditions & facilities

9.6/10

Eco-friendliness

Reviews

10/10 Excellent

Drew

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

10/10 Excellent

Blanca

Traveled with pets, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Great
Stayed 2 nights in Jan 2022

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

10/10 Excellent

Richard

Traveled with partner
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

10/10 Excellent

Troy

Stayed 3 nights in Sep 2021

10/10 Excellent

Lynda

Traveled with family
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

10/10 Excellent

Verified traveler

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

8/10 Good

Verified traveler

Traveled with partner
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

10/10 Excellent

Verified traveler

Traveled with partner, Traveled with pets
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

10/10 Excellent

Verified traveler

Stayed 1 night in Mar 2021