Title: Book the Best BEACH RESORTS in Great Oak Landing, MD from CA $156 - Great Oak Landing Hotels on the Beach| Expedia.ca

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# Find beach hotels in Great Oak Landing, MD from CA $156

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## Check availability on Great Oak Landing Beach Hotel

Tonight

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=3000045661&startDate=2025-12-14&endDate=2025-12-15&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

Tomorrow

[Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=3000045661&startDate=2025-12-15&endDate=2025-12-16&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000045661&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000045661&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach)

## Our top choices for Great Oak Landing beach hotels

![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lodge at Great Oak Landing

[](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

Chestertown

7.8/10

Good

(77)

"Very nice rooms, "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephania

CA $136

CA $156 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29&regionId=3000045661&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true)

## Top Great Oak Landing Hotel Reviews

## Frequently asked questions

### How much does a beach hotel in Great Oak Landing cost?

### Which area of Great Oak Landing is best to stay in for beaches?

> This central area offers direct access to the sandy shores of Great Oak Beach, which is a private beach for resort guests. You'll find most of the resort's amenities here, including dining options and recreational activities, all within a short walk of the waterfront. It's a convenient location for anyone looking to spend their days by the water.
> 
>   
> For couples looking for a relaxing beach holiday, this area is ideal. You can enjoy strolls along the beach, sunbathe, or take part in water sports right on your doorstep.

### What is the best time of year to stay in a beach hotel in Great Oak Landing?

> This period sees a bustling atmosphere around the resorts and along the waterfront, with all beach facilities and activities fully operational. Families, in particular, will find this a fantastic time for a beach holiday, with plenty of opportunities for swimming, sailing, and building sandcastles. It's also when many local events and outdoor concerts take place, adding to the vibrant summer experience.
> 
>   
> As another option, September is a great alternative for a beach hotel stay. The weather remains pleasantly warm, with average temperatures still in the low to mid-20s, making it excellent for relaxing on the sand or enjoying a leisurely stroll along the shore.

### How can I save on a beach hotel in Great Oak Landing with Expedia?

### Is it cheaper to book flights and a beach hotel in Great Oak Landing as a package?

### Can I cancel my beach hotel reservation on Expedia?

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