Flagler Vacations from $486

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The Latest Flagler vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
Northside Breck
Save 100% on your flight
Price was $727, price is now $486 per person
$486
per person
Jul 17 - Jul 20
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to Denver (DEN)
9.6/10 Exceptional! (1,138 reviews)
This is a great location... we enjoyed staying here. There was no decent hot breakfast on-site. We were surprised that we had to clean up the room (take out trash, take out linens, etc).

Reviewed on May 10, 2026

Glenwood Springs Inn

Glenwood Springs Inn

2 out of 5
Downtown
Price was $1,432, price is now $709 per person
$709
per person
Jul 14 - Jul 21
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Denver (DEN)
9/10 Wonderful! (1,575 reviews)
Clean room. Great location

Reviewed on May 11, 2026

A-Lodge Boulder

A-Lodge Boulder

3 out of 5
Save 100% on your flight
Price was $884, price is now $565 per person
$565
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Houston (IAH) to Denver (DEN)
8.8/10 Excellent! (1,006 reviews)
Staff was amazing we definitely did our research so we knew that it would be more of camper/hostel/hiking hotel. It's seen a lot of wear. The skylight above the beds is tough it stops the room from being dark in the morning which is really unfortunate. Loved the space and would stay again

Reviewed on May 1, 2026

The Residences at Main Street Station, Breckenridge

The Residences at Main Street Station, Breckenridge

4 out of 5
Historic District
Save 100% on your flight
Price was $921, price is now $603 per person
$603
per person
Jun 18 - Jun 21
just found
Roundtrip flight included
Houston (IAH) to Denver (DEN)
8.8/10 Excellent! (166 reviews)
The pool/hot tub and fitness center need to be upgraded. They are outdated and showing their age.

Reviewed on May 8, 2026

Boulder University Inn

Boulder University Inn

2.5 out of 5
University Hill
Save 100% on your flight
Price was $1,024, price is now $679 per person
$679
per person
Jun 25 - Jul 1
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Denver (DEN)
8.6/10 Excellent! (1,007 reviews)
Great staff, comfortable beds, and a perfect central location. On the downside, the window faced a common walkway, forcing us to keep the blinds closed for privacy. This made the room feel a bit dark and closed-in. Additionally, the AC was quite noisy. Traffic was also a bit noisy, which prevented us from opening a window.

Reviewed on May 9, 2026

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Flagler Hotel Deals

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
Claremont Inn & Winery

Claremont Inn & Winery

3.5 out of 5
800 Claremont Dr Stratton CO
$357 nightly
The price is $385 total per night from May 12 to May 13
$385 total
May 12 - May 13
Total with taxes and fees
8.8/10 Excellent! (172 reviews)
The Claremont Inn and Winery is ALWAYS EXCELLENT!

Reviewed on Jan 15, 2026

Claremont Inn & Winery
Comfy, quiet rustic lodge with game room, bar, dining room & full XL kitchen

Comfy, quiet rustic lodge with game room, bar, dining room & full XL kitchen

Joes CO
$190 nightly
The price is $196 total per night from May 12 to May 13
$196 total
May 12 - May 13
Total with taxes and fees
10/10 Exceptional! (5 reviews)
The property was beautiful and well maintained. The owner was super responsive and amazing! So excited to book another trip out here sooner than later!

Reviewed on Sep 2, 2025

Comfy, quiet rustic lodge with game room, bar, dining room & full XL kitchen
See all 3 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.

Find the Best Flagler Vacation Packages

Flagler Essential Information

Language
English
Currency
U.S dollars
Population
560

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Frequently asked questions

How much does a Flagler vacation package cost?
You can pick up a vacation package to this top destination from $486 on Expedia. But how much your vacation to Flagler costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Flagler?
January, February and April are the best times to search for cheap Flagler vacation packages. Traveling in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Flagler?
With a well-organized travel plan, you can easily tick off the most popular Flagler attractions in a few days. But if you prefer to explore off the beaten track or take day trips, think about booking your Flagler vacation for longer.
How to find the best Flagler package deals?
Use Expedia's filter tool to help you find some unbeatable Flagler package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Flagler package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Flagler vacation as a package?
You can enjoy significant savings on your Flagler escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Flagler?
Enjoy incredible discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Flagler vacation.
Does Expedia offer Book Now, Pay Later Flagler vacation packages?
Jet off on your perfect escape to Flagler with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next paycheck — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.