Great Oak Landing Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Great Oak Landing Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
Price was CA $1,268, price is now CA $1,190 per person
CA $1,190
per person
Jan 17 - Jan 23
found 3 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Salisbury (SBY)
8.6/10 Excellent! (990 reviews)
Convenient location, friendly staff, clean

Reviewed on Nov 8, 2026

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
Price was CA $1,450, price is now CA $1,363 per person
CA $1,363
per person
Dec 13 - Dec 19
found 3 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Salisbury (SBY)
7.2/10 Good! (511 reviews)

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Great Oak Landing Hotel Deals

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is CA $152 per night from Nov 15 to Nov 16
CA $152
CA $174 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (129 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."

Reviewed on Nov 8, 2026

The Lodge at Great Oak Landing
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Nov 15 to Nov 16
CA $95
CA $110 total
Nov 15 - Nov 16
includes taxes & fees
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 18 to Nov 19
CA $151
CA $177 total
Nov 18 - Nov 19
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"After a stressful return home from vacation the staff her mainly the front desk staff with their professional skills took care of my needs and gave me peace and joy"

Reviewed on Nov 9, 2026

Best Western Plus Hotel & Conference Center
See all 349 properties in Great Oak Landing
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.
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Frequently asked questions

How much does a Great Oak Landing vacation package cost?
Offering great value package deals from CA $1,190 on Expedia, you'll be thrilled with how little a vacation to Great Oak Landing costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Great Oak Landing?
To pick up cheap Great Oak Landing vacation packages, plan your trip outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability for flights and hotels.
How many days is enough for Great Oak Landing?
With a well-organized travel plan, you can easily hit the top Great Oak Landing attractions in a few days. But if you'd like to discover lesser-known spots or go on day trips, think about booking your Great Oak Landing vacation for longer.
How to find the best Great Oak Landing package deals?
Begin your search for a Great Oak Landing package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Great Oak Landing package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Great Oak Landing getaway off to a flying start.
Is it cheaper to book a Great Oak Landing vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can customize your Great Oak Landing getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Great Oak Landing?
If you've got your Great Oak Landing travel dates confirmed, book as early as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Great Oak Landing?

  1. Choose when to get away: Check your schedule and get packing. Your favourite time of year and the activities on offer will also help you decide when to escape to Great Oak Landing.
  2. Set a budget: Consider costs such as flights, transportation and food when calculating how much to put aside for your trip to Great Oak Landing. Then, pick a hotel that fits your budget, whether that's a low-cost option or a more luxurious getaway.
  3. Work out your trip length: Consider how much time you want to spend exploring Great Oak Landing. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Great Oak Landing vacation package.

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