Title: Great Oak Landing Vacation Packages & Trips 2025/2026 from CA $983 | Expedia.ca

  

[Hotels in Great Oak Landing](https://expedia.ca/Great-Oak-Landing-Hotels.d3000045661.Travel-Guide-Hotels)[Vacation Rentals in Great Oak Landing](https://expedia.ca/Great-Oak-Landing-Vacation-Rentals.d3000045661.Travel-Guide-VacationRentals)[Great Oak Landing Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Oak-Landing.d3000045661.Car-Rental-Guide)

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# Great Oak Landing Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

-   ## 
    
    Plan, book, travel with confidence
    

### 

Better together

Save up to CA $1,096 when you book a flight and hotel together\*

### 

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

### 

Rest easy

Plan, book, and manage your trip all in one place

## Top Great Oak Landing Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Gold Leaf Hotel of Dewey - Rehoboth Beach](https://images.trvl-media.com/lodging/18000000/17450000/17444200/17444119/1e642696_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Gold Leaf Hotel of Dewey - Rehoboth Beach

CA $983

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8.8/10 Excellent! (1,013 reviews)

Very friendly staff. Numerous restaurants within walking distance. Have to try Starboard Raw and Starboard Claw.

Reviewed on Sep 23, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17444119&paandie=true&dealMarker=ZOtnRC7kaMZpY62rOJlPWFHx4ZdgNR6prHVLTQ23QVTc-EqqugAkrtiWrzw9nTR8)

![Hyatt Place Dewey Beach](https://images.trvl-media.com/lodging/7000000/6100000/6099400/6099301/9ad04713_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Dewey Beach

CA $1,142

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8.8/10 Excellent! (1,006 reviews)

Wonderful hotel in Dewey beach, staff are super friendly and it is nicely located walking distance to beach.

Reviewed on Sep 6, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6099301&paandie=true&dealMarker=ZOtnRC7kaMZpY62rOJlPWFHx4ZdgNR6prHVLTQ23QVS7BZDpJeQuFruXMDMXRI7X)

![The Inn at Lewes](https://images.trvl-media.com/lodging/10000000/9110000/9109000/9108984/6fceeb00_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Inn at Lewes

CA $987

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

6.2/10 (93 reviews)

The staff was very helpful.The gentleman even helped me get into My room and I really appreciate that

Reviewed on Jun 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=9108984&paandie=true&dealMarker=ZOtnRC7kaMZpY62rOJlPWFHx4ZdgNR6prHVLTQ23QVTjUfXw8kUB08Weo0n4LN_e)

![Comfort Inn & Suites Milford](https://images.trvl-media.com/lodging/2000000/1180000/1178300/1178282/2bacc227_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Comfort Inn & Suites Milford

CA $1,079

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8/10 Very Good! (596 reviews)

Clean room. Excellent staff

Reviewed on Sep 8, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1178282&paandie=true&dealMarker=ZOtnRC7kaMZpY62rOJlPWFHx4ZdgNR6prHVLTQ23QVT2wxdZZiaJkIHYIckYzIH4)

![Hampton Inn Milford](https://images.trvl-media.com/lodging/4000000/3650000/3645000/3644980/3ed7ec07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn Milford

CA $1,087

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Salisbury (SBY)

8.6/10 Excellent! (961 reviews)

Very nice clean property amazing staff bit a lot of thing around but great if you have a car

Reviewed on Sep 22, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YOW&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3644980&paandie=true&dealMarker=ZOtnRC7kaMZpY62rOJlPWFHx4ZdgNR6prHVLTQ23QVQxZanDWQiU1ZH_pvvTifNM)

## Ready to book your vacation to Great Oak Landing?

Choose your dates

## Great Oak Landing Hotel Deals

![The Lodge at Great Oak Landing](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd, Chestertown, MD

Fully refundableReserve now, pay when you stay

CA $183

CA $203 total

Sep 24 - Sep 25

includes taxes & fees

8/10 Very Good! (68 reviews)

"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!!"

Reviewed on Sep 5, 2025

[](https://expedia.ca/Hotel-Search?startDate=24%2F09%2F2025&endDate=25%2F09%2F2025&selected=96826266&PinnedHotelID=96826266&HadPinnedHotel=true&regionId=3000045661)

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore, MD

Fully refundableReserve now, pay when you stay

CA $148

CA $173 total

Sep 28 - Sep 29

includes taxes & fees

7.6/10 Good! (1,008 reviews)

"The staff were professional and friendly."

Reviewed on Sep 21, 2025

[](https://expedia.ca/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=10260&PinnedHotelID=10260&HadPinnedHotel=true&regionId=3000045661)

![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Garden Inn Baltimore/White Marsh

5015 Campbell Boulevard, Baltimore, MD

Fully refundableReserve now, pay when you stay

CA $141

CA $162 total

Sep 24 - Sep 25

includes taxes & fees

7.8/10 Good! (1,014 reviews)

"everyone was so nice! and helpful! the food was good!"

Reviewed on Sep 18, 2025

[](https://expedia.ca/Hotel-Search?startDate=24%2F09%2F2025&endDate=25%2F09%2F2025&selected=433663&PinnedHotelID=433663&HadPinnedHotel=true&regionId=3000045661)

[See all 356 properties in Great Oak Landing](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=24%2F09%2F2025&endDate=25%2F09%2F2025&regionId=3000045661)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Great Oak Landing

#### Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

[](https://expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction)

#### Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

[](https://expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction)

## Explore a world of travel with Expedia

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)