Chipley Vacations from $487

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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.
Bikini Beach Resort

Bikini Beach Resort

2.5 out of 5
Long Beach
Price was $624, price is now $487 per person
$487
per person
May 27 - May 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
7.4/10 Good! (2,212 reviews)
The bar wasn't opened and the rooms were decent,. Location is top notch and super close tot the beach with chairs and umbrellas outside. The pool was open and has plenty of seating.

Reviewed on Apr 9, 2026

Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool, Hot Tub & Tennis

Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool, Hot Tub & Tennis

4 out of 5
Price was $1,167, price is now $865 per person
$865
per person
Jun 12 - Jun 15
found 12 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Panama City (ECP)
No reviews
Sandbar Serenade by Avantstay Beachside Home + Pool + Tennis Court + Beach Access + Near Pier Park

Sandbar Serenade by Avantstay Beachside Home + Pool + Tennis Court + Beach Access + Near Pier Park

3 out of 5
Price was $1,130, price is now $840 per person
$840
per person
Jun 12 - Jun 15
found 12 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Panama City (ECP)
No reviews
Beachcomber Beachfront Hotel, a By The Sea Resort

Beachcomber Beachfront Hotel, a By The Sea Resort

2.5 out of 5
Price was $780, price is now $601 per person
$601
per person
May 27 - May 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
6.4/10 (1,128 reviews)
The internet was down most of the nights, One of the beds was broken, and no pots or pans, only lids. It was nice for the price ! The pool was the kids favorite!

Reviewed on Apr 9, 2026

Seahaven Beach Hotel

Seahaven Beach Hotel

2 out of 5
Price was $621, price is now $487 per person
$487
per person
May 27 - May 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
6.2/10 (1,966 reviews)
I dont have a pet, its dissent..

Reviewed on Apr 9, 2026

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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

4/5(19 reviews)

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
$54 nightly
The price is $60 total per night from Apr 16 to Apr 17
$60 total
Apr 16 - Apr 17
Total with taxes and fees
8/10 Very Good! (2,331 reviews)
Property was great as always

Reviewed on Apr 9, 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
$61 nightly
The price is $69 total per night from Apr 12 to Apr 13
$69 total
Apr 12 - Apr 13
Total with taxes and fees
7.2/10 Good! (1,510 reviews)
This property was beyond gross, WE DID NOT STAY, the place is not under renovation as stated online …mold was in the bathroom with an awful smell of urine, the refrigerator was nasty black mold in the fridge. My family have asthma & respiratory issues me and my daughter became sick after being in ...

Reviewed on Apr 9, 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
$147 nightly
The price is $166 total per night from Apr 16 to Apr 17
$166 total
Apr 16 - Apr 17
Total with taxes and fees
8.8/10 Excellent! (2,540 reviews)
Ok

Reviewed on Apr 9, 2026

Hampton Inn & Suites Panama City Beach-Beachfront
See all 7,797 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 $487 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.