Flagler 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 Flagler Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Maven Hotel at Dairy Block

The Maven Hotel at Dairy Block

4.5 out of 5
LoDo
Price was CA $2,723, price is now CA $1,927 per person
CA $1,927
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Denver (DEN)
9.4/10 Exceptional! (1,114 reviews)

One Ski Hill Place, a RockResort, by Vail Resorts

One Ski Hill Place, a RockResort, by Vail Resorts

4 out of 5
Peak 8
Price was CA $13,295, price is now CA $9,257 per person
CA $9,257
per person
Dec 19 - Dec 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
9.2/10 Wonderful! (936 reviews)

The Oxford Hotel

The Oxford Hotel

4.5 out of 5
LoDo
Price was CA $2,768, price is now CA $1,937 per person
CA $1,937
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Denver (DEN)
9.6/10 Exceptional! (1,078 reviews)
This hotel was very disappointing. I arrived and found a note on the counter indicating that they were under construction and the climate control was not working in the rooms. They brought a big box fan that was very noisy. The shower was old with low water pressure. The floorboards under the rug were creaky. I couldn’t find the hairdryer—and the front desk person didn’t have extras or know where I should look (it turned out to be in a box that looked like a safe that was sitting on the shelf in the closet). The gym nextdoor which they have a partnership with was an hour and a half from opening with I arrived at 5:15a to work out before my day of meetings started. (And a guest was checking out early at that hour after getting no sleep.) Not a good stay.

Reviewed on Nov 13, 2026

Village at Breckenridge, A Vail Resorts Property

Village at Breckenridge, A Vail Resorts Property

3 out of 5
Historic District
Price was CA $4,060, price is now CA $2,850 per person
CA $2,850
per person
Dec 19 - Dec 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
8.4/10 Very good! (2,163 reviews)

Laurelwood Condominiums

Laurelwood Condominiums

3 out of 5
Price was CA $4,407, price is now CA $3,185 per person
CA $3,185
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Denver (DEN)
9.2/10 Wonderful! (1,577 reviews)
Beautiful property. The room was unbelievably awesome. Will definitely reserve there again.

Reviewed on Nov 14, 2026

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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
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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 $1,927 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.