Sleepfare

The Lodge at Great Oak Landing

★★★ 22170 Great Oak Landing Rd, Chestertown, Maryland, 21620, Chestertown, US

7.6 guest rating· 48 reviews

About this hotel

Golf Course and Private Beach

Practice your swing on the golf course or soak up the sunshine on the private beach.

Amenities and Dining

Enjoy a satisfying meal at The Landing at Great Oak. The lodge features complimentary wireless internet access, gift shops/newsstands, and a picnic area. Wrap up your day with a drink at the bar/lounge.

Convenient Facilities

Featured amenities include express check-out, laundry facilities, and ATM/banking services. Free self-parking is available onsite.

Start your beachfront getaway with us at The Lodge at Great Oak Landing.

Rooms & rates

Pick your dates. Prices are live, not cached.

Standard Room, 2 Double Beds

Sleeps 4 · 2× Double bed

  • Private bathroom
  • Free WiFi
  • Telephone
  • Hair dryer
  • Interconnected room(s) available

<p><strong>2 Double Beds</strong></p><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower/tub combination, a hair dryer, and towels</p><p><b>Practical</b> - Phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Room, 1 Queen Bed, Accessible

Sleeps 2 · Queen Bed

  • Private bathroom
  • Free WiFi
  • Telephone
  • Hair dryer
  • Interconnected room(s) available

<p><strong>1 Queen Bed</strong></p><p>Located on the ground floor</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower/tub combination, a hair dryer, and towels</p><p><b>Practical</b> - Phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Accessibility</b> - Wheelchair accessible</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Room, 1 King Bed with Sofa bed, Marina View

Sleeps 3 · King bed, Sofa bed

  • Private bathroom
  • Free WiFi
  • Telephone
  • Hair dryer
  • Interconnected room(s) available

<p><strong>1 King Bed and 1 Twin Sofa Bed</strong></p><p>Located on the top floor with water views</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower/tub combination, a hair dryer, and towels</p><p><b>Practical</b> - Phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Standard Room, 1 King Bed

Sleeps 2 · King bed

  • Private bathroom
  • Free WiFi
  • Telephone
  • Hair dryer
  • Interconnected room(s) available

<p><strong>1 King Bed</strong></p><p>Located on the top floor</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower/tub combination, a hair dryer, and towels</p><p><b>Practical</b> - Phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Room, 2 Queen Beds, Marina View

Sleeps 4 · 2× Queen Bed

  • Private bathroom
  • Free WiFi
  • Telephone
  • Hair dryer
  • Interconnected room(s) available

<p><strong>2 Queen Beds</strong></p><p>Located on the top floor with water views</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower/tub combination, a hair dryer, and towels</p><p><b>Practical</b> - Phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Suite

Sleeps 5 · King bed, Sofa bed, Sofa bed

  • Private bathroom
  • Free WiFi
  • Shower
  • Telephone
  • Hair dryer

<p><strong>1 King Bed, 1 Twin Sofa Bed and 1 Double Sofa Bed</strong></p><p>Furnished balcony with marina views</p><br/><p><b>Layout</b> - Bedroom, living room, and sitting area</p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Refrigerator, microwave, and freezer</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, a hair dryer, and towels</p><p><b>Practical</b> - Iron/ironing board and phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Room, 1 King Bed

Sleeps 2 · King bed

  • Private bathroom
  • Free WiFi
  • Telephone
  • Hair dryer
  • Interconnected room(s) available

<p><strong>1 King Bed</strong></p><p>Located on the ground floor</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi 25+ Mbps </p><p><b>Entertainment</b> - 36-inch flat-screen TV with cable channels</p><p><b>Food & Drink</b> - Mini-fridge</p><p><b>Sleep</b> - Bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower/tub combination, a hair dryer, and towels</p><p><b>Practical</b> - Phone</p><p><b>Comfort</b> - Climate-controlled heating and air conditioning</p><p><b>Need to Know</b> - Housekeeping on request, toothbrush and toothpaste not available</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Amenities

  • Free WiFi
  • Fence around pool
  • Outdoor pool - seasonal
  • Pool sun loungers
  • Pool umbrellas
  • 24-hour fitness facilities
  • Free self parking
  • Wheelchair accessible parking
  • Wheelchair-accessible van parking
  • Wheelchair-accessible on-site restaurant
  • Beach sun loungers
  • Beach volleyball on site
  • Direct access to private beach
  • Private beach nearby
Show all 35 amenities
  • Accessible shuttle
  • ATM/banking
  • Charcoal grill
  • Coin laundry on site
  • Dock
  • Express check-in/check-out
  • Express check-out
  • Firepit
  • Firewood (free)
  • Front entrance ramp
  • Gas grill
  • Gift shops or newsstand
  • Housekeeping on request
  • No accessible shuttle
  • Outdoor entertainment area
  • Outdoor furniture
  • Picnic area
  • Playground on site
  • Smoke-free property
  • Upper floors accessible by stairs only
  • Walkway to water

Location

© OpenStreetMap contributors

22170 Great Oak Landing Rd, Chestertown, Maryland, 21620, Chestertown, US

What guests say7.648 reviews

+ Friendly staff+ Great views+ Comfortable bed− Dirty rooms− WiFi issues− Outdated furnishings
Cleanliness5.4
Service8.9
Location8.9
Room Quality6.4
Amenities7.4
Value for Money6.9

Guest review

4.0

WIFI did not work. As such WIFI TV apps (Netflix, Prime, etc) were unavailable.

Steve · 2025-09-27

Guest review

2.0

Reserved 2 rooms but only given code for one. No staff on property or reachable by phone to address situation. Waiting around and hoping for the best. And it smells bad and WiFi doesn’t work.

George · 2025-09-27

Guest review

10.0

Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!

Melissa · 2025-09-05

Guest review

6.0

Outdated. Room had a peculiar odor.

Jennifer · 2025-08-22

Guest review

6.0

Considering the time of year, I expected it to be a bit pricey, but I thought that the room and amenities would be better considering the price

jamie · 2025-08-19

Dirty and gross

2.0

Only pro was the bed was comfortable. The room was dirty and everything was old and very outdated. Floorboards, doors and fixtures were dirty. Shower floor was gross. Walls had rust, dirt and holes. Deck was unkempt and dirty. Did not eat there because I didn’t trust the cleanliness of their kitchen based on the room.

Todd · 2025-08-18

Good to know

The seasonal pool will be open from May 23 to September 18.

Pool access available from 10:00 AM to 8:00 PM.

Only registered guests are allowed in the guestrooms.

The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation.

Cashless payment methods are available for all transactions.

›Pets

Pets not allowed

›Sustainability Certifications

Property confirms they are implementing guest safety measures

›Children and extra beds

No rollaway/extra beds available

›Noise policy

Noise-free rooms not guaranteed

›Check-in & Check-out

Contactless check-out is available

›General

Gap period enforced between guest stays - 48 hours

›General

Cashless transactions are available

›Accessibility

No elevators

›General

Bed sheets and towels are washed at a temperature of at least 60°C/140°F

›General

Property is cleaned with disinfectant

›Guest type

LGBTQ friendly

›General

Professional property host/manager

›Check-in & Check-out

Contactless check-in is available

›Children and extra beds

No cribs (infant beds) available

›Sustainability Certifications

Property confirms they are implementing enhanced cleaning measures

›General

Commonly-touched surfaces are cleaned with disinfectant