Chipley Vacations from $881

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Your Chipley Vacation

Experience the unique character and personality of Chipley with a tailor-made Chipley vacation package. From its small-town feel to its friendly locals and beyond, you'll never have a dull moment in this city. Your trip to Chipley has to include a little sightseeing. Falling Waters State Park is a good place to start. Expedia is here to help you escape your routine. Tailor your vacation to Chipley to suit your style of travel, whatever that may be!

The Latest Chipley vacation packages

Price found within the past 48 hours. Click for updated prices.
Landing Apartments - Freeport Near Santa Rosa Beach

Landing Apartments - Freeport Near Santa Rosa Beach

3 out of 5
Price was $1,239, price is now $881 per person
$881
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Panama City (ECP)
No reviews
Blue Marlin by Avantstay Beachfront w/ Views, Pool Access, Beach Chairs

Blue Marlin by Avantstay Beachfront w/ Views, Pool Access, Beach Chairs

3 out of 5
Sunnyside
Price was $4,123, price is now $2,816 per person
$2,816
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Panama City (ECP)
No reviews
Bellview by Avantstay Gorgeous Home w/ Multiple Balconies & Living Areas

Bellview by Avantstay Gorgeous Home w/ Multiple Balconies & Living Areas

3.5 out of 5
Sunnyside
Price was $5,127, price is now $3,543 per person
$3,543
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Panama City (ECP)
No reviews
Newly Renovated! 2-min Walk to the Beach The Coastal Cottage by Avantstay

Newly Renovated! 2-min Walk to the Beach The Coastal Cottage by Avantstay

3 out of 5
Sunnyside
Price was $3,980, price is now $2,758 per person
$2,758
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Panama City (ECP)
No reviews
Sandy Pelican by Avantstay Exclusive Beach Access + Private Pool + Firepit + Balcony Sunset Views

Sandy Pelican by Avantstay Exclusive Beach Access + Private Pool + Firepit + Balcony Sunset Views

3 out of 5
Seacrest
Price was $4,806, price is now $3,444 per person
$3,444
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Panama City (ECP)
No reviews
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Discover the most popular places to visit in Chipley

waterfall Falling Waters State Park green foliage limestone

Falling Waters State Park

Commune with nature and explore the great outdoors at Falling Waters State Park during your travels in Chipley. Stroll along the lakeside or discover the area's waterfalls.

Falling Waters State Park

Chipley Hotel Deals

Palmetto Beachfront Hotel, a By the Sea Resort

Palmetto Beachfront Hotel, a By the Sea Resort

2 out of 5
17255 Front Beach Road Panama City Beach FL
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $72 total per night from Apr 14 to Apr 15
$72 total
Apr 14 - Apr 15
Total with taxes and fees
8/10 Very Good! (2,304 reviews)
Everything Was Good It’s Just Everytime I Turned Around Money Was Trying To Come Off My Card For Something Concerning This Property. I Will Not Stay There Again Only Because I Have People Who Like To Have There Nicotine & There Is NO SMOKING AT ALL On The Balcony Or Anything. Beautiful Beach View ...

Reviewed on Apr 2, 2026

Palmetto Beachfront Hotel, a By the Sea Resort
Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

2.5 out of 5
12525 Front Beach Rd Panama City Beach FL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Apr 12 to Apr 13
$85 total
Apr 12 - Apr 13
Total with taxes and fees
7.2/10 Good! (1,475 reviews)
Staff was friendly. View and Location were perfect. Right on the Beach. You can tell its an older Hotel though.

Reviewed on Apr 2, 2026

Chateau Beachfront Hotel, A By The Sea Resort
Hampton Inn & Suites Panama City Beach-Beachfront

Hampton Inn & Suites Panama City Beach-Beachfront

2.5 out of 5
15505 Front Beach Road Panama City Beach FL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $152 total per night from Apr 15 to Apr 16
$152 total
Apr 15 - Apr 16
Total with taxes and fees
8.8/10 Excellent! (2,522 reviews)
The TV did not work the whole time I was there went to the front desk notified them they did absolutely nothing but him yeah sheet of paper like I don't know how to turn on a TV and connect to the internet they did not try to come up now one time to troubleshoot it to see what was going on with it ...

Reviewed on Apr 3, 2026

Hampton Inn & Suites Panama City Beach-Beachfront
See all 7,789 properties in Chipley
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 Chipley Vacation Packages

Chipley Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
65ºF
Max Temp Summer
90ºF

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Frequently asked questions

How much does a Chipley vacation package cost?
You'll find cheap prices from $881 on Expedia for your Chipley escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Chipley costs.
What are the cheapest months to go to Chipley?
If you're hoping to snag a cheap Chipley vacation package, consider visiting in August, September and October. You're likely to find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Chipley?
The ideal duration for your Chipley vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to hit all the top sights and discover some hidden gems along the way.
How to find the best Chipley package deals?
Begin your search for a Chipley package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some 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 huge savings. If you don't find the ideal Chipley package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chipley getaway off to a flying start.
Is it cheaper to book a Chipley vacation as a package?
You can enjoy significant savings on your next Chipley escape by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chipley?
If you're considering an impromptu Chipley vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Chipley vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Chipley trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.

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