
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
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
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



Stay near popular Chipley attractions
Chipley Hotel Deals

Palmetto Beachfront Hotel, a By the Sea Resort
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

Radisson Beachfront Hotel - Panama City Beach
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

Chateau Beachfront Hotel, A By The Sea Resort
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.





















