Chipley Vacations from $1,339

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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.
The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,736, price is now $1,339 per person
$1,339
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
9.4/10 Exceptional! (224 reviews)
This was our first time staying at The Pearl. It was beautiful, clean and relaxing. The staff were wonderful, friendly and helpful. We had great access to the beach that was less than a 5 minute walk.

Reviewed on Jun 25, 2026

South Shore 30A by Avantstay Gulf View Pool

South Shore 30A by Avantstay Gulf View Pool

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,995, price is now $2,252 per person
$2,252
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Panama City (ECP)
6/10 (1 review)
The property has an amazing location, but at a price that you sleep on a dirty bed. You can notice the level of cleanliness that the AC filter was dirty. Check your beds before going to bed. It had lots of hairs from previous guest

Reviewed on Oct 2, 2025

3 Ensuite Bedrooms, Porches & BBQ Near Inlet Beach 30A Ciel Bleu by Avantstay

3 Ensuite Bedrooms, Porches & BBQ Near Inlet Beach 30A Ciel Bleu by Avantstay

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,762, price is now $1,352 per person
$1,352
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
No reviews

Steps to Rosemary Beach, Pool, Patio w/ Firepit The Salty Perch by Avantstay

Steps to Rosemary Beach, Pool, Patio w/ Firepit The Salty Perch by Avantstay

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,951, price is now $1,529 per person
$1,529
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Panama City (ECP)
No reviews

Walk to Seacrest Beach, Resort Pool Modern 3bdr Free Wheelin by Avantstay

Walk to Seacrest Beach, Resort Pool Modern 3bdr Free Wheelin by Avantstay

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,718, price is now $1,353 per person
$1,353
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Panama City (ECP)
No reviews

Don't see what you're looking for?
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Stay near popular Chipley attractions

A waterfall cascading down a moss-covered rock in a forested area.

Falling Waters State Park

8.6/10 (48 reviews)
Florida's tallest waterfall plunges 73 feet into a cylindrical sinkhole before disappearing underground. Stroll the boardwalks through pine forests and fern-covered sinkholes for the most dramatic views after rainfall.
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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
$118 nightly
The price is $133 total per night from Jul 5 to Jul 6
$133 total
Jul 5 - Jul 6
Total with taxes and fees
7.8/10 Good! (2,626 reviews)
"I was glad that I had clarified that I was on the beach side of the resort. Several times when I was in the lobby, there were upset guests checking in who thought they were beachside but were really across the street. Overall, the location is great. It is not a modern or well-kept resort but is practical ..."

Reviewed on Jul 1, 2026

Palmetto 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
$178 nightly
The price is $202 total per night from Jul 27 to Jul 28
$202 total
Jul 27 - Jul 28
Total with taxes and fees
7/10 Good! (2,815 reviews)
"Todo bien"

Reviewed on Jun 30, 2026

Radisson Beachfront Hotel - Panama City Beach
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
$147 nightly
The price is $166 total per night from Jul 28 to Jul 29
$166 total
Jul 28 - Jul 29
Total with taxes and fees
7/10 Good! (1,871 reviews)
"The front desk staff was very helpful, the room was clean and great atmosphere at the pool. I just wish the parking lot wasn't a paid to park because even though we had free parking for having reservations it doesn't feel fair that we should park across the street."

Reviewed on Jul 1, 2026

Chateau Beachfront Hotel, A By The Sea Resort
See all 7,739 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 $1,339 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.