Cortland Vacation Packages

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Your Cortland Vacation

Spend less time planning and more time having exciting adventures with a Cortland vacation package. The neighborhood of Timberline, which is good for skiing and hiking, makes an excellent base for your city escape. Fill your schedule with tours of Blackwater Falls State Park, Canaan Valley Ski Resort and Blackwater Falls, some of the top attractions you simply have to see during your trip to Cortland. Whoever you're taking a break with and whatever the size of your budget, your ultimate Cortland vacation is just a few clicks away with Expedia.

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Cortland Hotel Deals

The Inn at Canaan

The Inn at Canaan

2.5 out of 5
6526 Appalachian Highway Davis WV
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Nov 10 to Nov 11
CA $174
CA $198 total
Nov 10 - Nov 11
includes taxes & fees
8.6/10 Excellent! (948 reviews)
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Reviewed on Nov 9, 2026

The Inn at Canaan
Hermitage Inn & Pub

Hermitage Inn & Pub

2.5 out of 5
203 Virginia Ave Petersburg WV
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Nov 10 to Nov 11
CA $258
CA $300 total
Nov 10 - Nov 11
includes taxes & fees
Hermitage Inn & Pub
Luxurious, rustic, private vacation home with great view.

Luxurious, rustic, private vacation home with great view.

Davis WV
The price is CA $375 per night from Nov 15 to Nov 16
CA $375
CA $806 total
Nov 15 - Nov 16
includes taxes & fees
10/10 Exceptional! (440 reviews)
"The owners are very responsive. The house and property are great. Excellent immenities."

Reviewed on Nov 8, 2026

Luxurious, rustic, private vacation home with great view.
See all 661 properties in Cortland
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Frequently asked questions

How much does a Cortland vacation package cost?
You can pick up a vacation package to this top destination on Expedia. But how much your vacation to Cortland costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Cortland?
If you'd like to score a cheap Cortland vacation package, consider travelling in January, February and April. You're likely to find better prices on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Cortland?
Cortland vacations come in all shapes and sizes, but to really get a feel for this destination, we think 2 days is a good ballpark. With this timeframe, you can fit in major attractions like Canaan Valley Resort State Park and Canaan Valley Ski Resort as well as underrated gems. Don't miss out on neighbourhoods such as Timberline and Old Timberline either. If you plan wisely, you can even allow for a day trip from Cortland too.
How to find the best Cortland package deals?
Use Expedia's filters to help you find some of the best Cortland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Cortland package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Cortland vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights separately. Better still, you can tailor your Cortland getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Cortland?
If you have your Cortland vacation dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Cortland?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Cortland.
  2. Plan your budget wisely: On top of the price of your accommodations, you'll need to consider other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could arise during your trip to Cortland.
  3. Determine how many days away: Start by listing all the attractions you'd like to experience in Cortland. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your accommodations and airfare: After you've settled on your dates and duration, book the ideal Cortland vacation package for you.

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