Flagler Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 Flagler Vacation Deals

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

Laurelwood Condominiums

3 out of 5
Save 100% on your flight
Price was CA $4,634, price is now CA $3,177 per person
CA $3,177
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.2/10 Wonderful! (1,577 reviews)
Nice area, quite, didn't seem very busy which was nice. We appreciated the fully stocked kitchen supplies, has everything we could think to need to cook in. The grill was great and easy to use.

Reviewed on Nov 1, 2026

Residences at the Little Nell

Residences at the Little Nell

5 out of 5
Downtown Aspen
Save 100% on your flight
Price was CA $11,331, price is now CA $8,347 per person
CA $8,347
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.8/10 Exceptional! (185 reviews)

Viceroy Snowmass

Viceroy Snowmass

5 out of 5
Save 100% on your flight
Price was CA $6,528, price is now CA $4,827 per person
CA $4,827
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9/10 Wonderful! (971 reviews)

The Timberline Condominiums

The Timberline Condominiums

3 out of 5
Save 100% on your flight
Price was CA $5,057, price is now CA $3,742 per person
CA $3,742
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9/10 Wonderful! (941 reviews)

Hotel Jerome, Auberge Collection

Hotel Jerome, Auberge Collection

5 out of 5
Downtown Aspen
Price was CA $12,355, price is now CA $9,735 per person
CA $9,735
per person
Jan 20 - Jan 27
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (487 reviews)

Ready to book your vacation to Flagler?

 

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Flagler Hotel Deals

Travelodge by Wyndham

2 out of 5
700 Colorado Ave Stratton CO
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Travelodge by Wyndham
Claremont Inn & Winery

Claremont Inn & Winery

3.5 out of 5
800 Claremont Dr Stratton CO
9.2/10 Wonderful! (172 reviews)
"The Claremont Inn and Winery is ALWAYS EXCELLENT!"

Reviewed on Jan 15, 2026

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Claremont Inn & Winery
Travelodge by Wyndham Stratton

Travelodge by Wyndham Stratton

2 out of 5
700 Colorado Ave Stratton CO
Get rates
Travelodge by Wyndham Stratton
See all 4 properties in Flagler
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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Flagler vacation package cost?
Offering excellent value package deals from CA $3,177 on Expedia, you'll be surprised at how little a vacation to Flagler costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Flagler?
You can usually find reduced prices and better availability in January, February and April. Take a look at our cheap Flagler vacation packages and you could get some excellent off-season deals.
How many days is enough for Flagler?
The ideal duration for your Flagler vacation depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to tick off all the top sights and explore some hidden spots along the way.
How to find the best Flagler package deals?
Begin your search for a Flagler package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Flagler package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Flagler getaway off to a flying start.
Is it cheaper to book a Flagler vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Flagler vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Flagler?
If you've got your Flagler travel dates finalized, book as early as you can to grab some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Flagler?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Flagler.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Flagler.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Flagler. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Flagler vacation package that brings all your bookings together.

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