Chipley Vacations from $1,250

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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.
Beachfront Panama City Beach Stay With Gulf Views, Balconies, a King Suite, two Queens, and Twin Nook for 8 Guests The Shores Townhome by Avantstay

Beachfront Panama City Beach Stay With Gulf Views, Balconies, a King Suite, two Queens, and Twin Nook for 8 Guests The Shores Townhome by Avantstay

3 out of 5
Sunnyside
Price was $1,586, price is now $1,250 per person
$1,250
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Miami (MIA) to Panama City (ECP)
No reviews
WaterSound Inn

WaterSound Inn

4 out of 5
WaterSound Beach
Save 100% on your flight
Price was $1,854, price is now $1,297 per person
$1,297
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Miami (MIA) to Panama City (ECP)
9.4/10 Exceptional! (95 reviews)
It’s a beautiful option in a beautiful area

Reviewed on Dec 13, 2024

Sleeps 24 Beach Retreat w/ Pool, Rooftop Deck, Steps to Inlet Beach & Near Rosemary, Alys, Seacrest Dining & Shops The Palm 30A by Avantstay

Sleeps 24 Beach Retreat w/ Pool, Rooftop Deck, Steps to Inlet Beach & Near Rosemary, Alys, Seacrest Dining & Shops The Palm 30A by Avantstay

3 out of 5
Inlet Beach
Save 100% on your flight
Price was $4,646, price is now $3,380 per person
$3,380
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Miami (MIA) to Panama City (ECP)
No reviews
Totally Beachin by Avantstay Sleeps 18 Seacrest Beach

Totally Beachin by Avantstay Sleeps 18 Seacrest Beach

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $3,417, price is now $2,566 per person
$2,566
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Miami (MIA) to Panama City (ECP)
No reviews
Emerald Escape by Avantstay Walk to Beach

Emerald Escape by Avantstay Walk to Beach

3 out of 5
Price was $1,796, price is now $1,411 per person
$1,411
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Miami (MIA) to Panama City (ECP)
No reviews
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Discover the most popular places to visit in Chipley

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

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
$93 nightly
The price is $105 total per night from Nov 11 to Nov 12
$105 total
Nov 11 - Nov 12
Total with taxes and fees
8.6/10 Excellent! (2,067 reviews)
It was a very wide range of food. Three waffle makers was great because there was no lines.

Reviewed on Oct 24, 2025

Hampton Inn & Suites Panama City Beach-Beachfront
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
$64 nightly
The price is $72 total per night from Oct 28 to Oct 29
$72 total
Oct 28 - Oct 29
Total with taxes and fees
7/10 Good! (1,210 reviews)
Friendly staff

Reviewed on Oct 21, 2025

Chateau Beachfront Hotel, A By The Sea Resort
Radisson Beachfront Hotel - Panama City Beach

Radisson Beachfront Hotel - Panama City Beach

3 out of 5
15325 Front Beach Road, Panama City Beach, FL
Fully refundable
$85 nightly
The price is $96 total per night from Oct 29 to Oct 30
$96 total
Oct 29 - Oct 30
Total with taxes and fees
7/10 Good! (2,428 reviews)
beach access and the view

Reviewed on Oct 24, 2025

Radisson Beachfront Hotel - Panama City Beach
See all 7,845 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 $1,250 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.