Chipley Vacations from $467

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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.
Bluegreen's Bayside Resort and Spa

Bluegreen's Bayside Resort and Spa

4.5 out of 5
Price was $646, price is now $467 per person
$467
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Panama City (ECP)
7.2/10 Good! (299 reviews)
Great relaxing place to relax.

Reviewed on Aug 29, 2025

Camp Creek Inn

Camp Creek Inn

4 out of 5
Save 100% on your flight
Price was $1,346, price is now $963 per person
$963
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Panama City (ECP)
9.8/10 Exceptional! (112 reviews)
We loved it 100% thank you for all the service and care for my family

Reviewed on Sep 2, 2025

Halcyon Dayz by Avantstay New Build w/ Pool Access

Halcyon Dayz by Avantstay New Build w/ Pool Access

3 out of 5
Save 100% on your flight
Price was $2,778, price is now $2,069 per person
$2,069
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Panama City (ECP)
No reviews
Porch Paradise by Avantstay Private Pool Seacrest

Porch Paradise by Avantstay Private Pool Seacrest

3 out of 5
Seacrest
Save 100% on your flight
Price was $2,666, price is now $2,049 per person
$2,049
per person
Nov 25 - Nov 30
found 10 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Panama City (ECP)
No reviews
Beach Retreat w/ Sundeck, Golf Cart & Bikes Bungalow House by Avantstay

Beach Retreat w/ Sundeck, Golf Cart & Bikes Bungalow House by Avantstay

3 out of 5
Seacrest
Save 100% on your flight
Price was $2,397, price is now $1,851 per person
$1,851
per person
Nov 25 - Nov 30
found 10 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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

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
$63 nightly
The price is $72 total per night from Sep 21 to Sep 22
$72 total
Sep 21 - Sep 22
Total with taxes and fees
7.8/10 Good! (1,901 reviews)
"We enjoyed the pool and the easy access to the beach will be back next year"

Reviewed on Sep 16, 2025

Palmetto 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
$121 nightly
The price is $137 total per night from Sep 29 to Sep 30
$137 total
Sep 29 - Sep 30
Total with taxes and fees
8.6/10 Excellent! (1,976 reviews)
"Super convenient for the beach, I stay here often. This time the smoke from balconies made it unbearable to sit outside and enjoy the balcony! And the dogs in the room close to mine barked for 10 minutes straight everytime someone walked down the hall, shut a door, or any noise was heard. Made for ..."

Reviewed on Sep 16, 2025

Hampton Inn & Suites Panama City Beach-Beachfront
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 Sep 21 to Sep 22
$96 total
Sep 21 - Sep 22
Total with taxes and fees
7/10 Good! (2,375 reviews)
"Loved that it was a close walk or drive to restaurants. Parking was ample. Our room was nice & clean. We had a connecting room, and I was able to hear the baby next door crying. But it's a family friendly hotel so, to be expected. Other than that I had a great time!"

Reviewed on Sep 15, 2025

Radisson Beachfront Hotel - Panama City Beach
See all 7,796 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.

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Frequently asked questions

How much does a Chipley vacation package cost?
You'll find cheap prices from $467 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.