
Chipley Vacations from $1,352
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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.


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

The Pearl Hotel
Rosemary Beach
Save 100% on your flight
Price was $2,262, price is now $1,703 per person
$1,703
per person
Sep 16 - Sep 20
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


Steps to Private Beach Access Pool + Bikes Seacrest 30A
Rosemary Beach
Save 100% on your flight
Price was $3,284, price is now $2,525 per person
$2,525
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Panama City (ECP)
10/10 Exceptional! (1 review)
This house is well maintained and clean with comfortable beds and plenty of space for our family of five. There is definitely room for more people too. Each room has its own bathroom which makes getting ready for outings much easier. The house is located in the seacrest beach section of Rosemary Beach and is only a five minute walk to pool and 10 minute walk to beach. The pool lagoon area is beautiful with a cafe and bathrooms and plenty of seating for the month of August. The beach has a beautiful entrance and white sand with clear waters and chair/umbrellas to rent for the day. There is also a very good cafe steps up from beach called Crabby Steve’s high point. We walked everywhere in seacrest and proper Rosemary beach near the Pearl Hotel. We ate good meals every day. Lots of restaurants to try. This house did not have bikes included in our rental price. If this is important to you check out bike rental options before you go. Our family swam in pool and golf most of day, especially bc August weather brings so much heat and humidity to this area, and we got dressed nicely and walked to dinner in the evening and then walked to ice cream and shops before going back to house. We had quiet, quality family time.
Reviewed on Aug 27, 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
$127 nightly
The price is $143 total per night from Jul 5 to Jul 6
$143 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
$153 nightly
The price is $173 total per night from Jul 5 to Jul 6
$173 total
Jul 5 - Jul 6
Total with taxes and fees
7/10 Good! (1,870 reviews)
"Checking in at the front desk started out well with one lady and then I had to go to a different lady. She was very rude. Very unhelpful. They make it hard and complicated to check in because you have to do all this stuff on the tablet and then they have do some more on the computer then you have ..."
Reviewed on Jun 30, 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.





















