Chipley Vacations from $1,027

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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.
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
Save 100% on your flight
Price was $1,337, price is now $1,027 per person
$1,027
per person
May 31 - Jun 4
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
No reviews
The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,740, price is now $1,263 per person
$1,263
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Panama City (ECP)
9.6/10 Exceptional! (213 reviews)
Very OK hotel. We have stayed at the Fairmont across Canada and other really nice boutique hotels but The Pearl is average in comparison. No gym at this venue. Pool is smaller than those found at people’s homes. The room was very comfortable though. Shower is nice bug that’s about it. For what they charge, you are really getting a very average stay.

Reviewed on Apr 6, 2026

Newly Renovated! 2-min Walk to the Beach The Coastal Cottage by Avantstay

Newly Renovated! 2-min Walk to the Beach The Coastal Cottage by Avantstay

3 out of 5
Sunnyside
Save 100% on your flight
Price was $2,193, price is now $1,597 per person
$1,597
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $2,513, price is now $1,913 per person
$1,913
per person
May 28 - May 31
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Panama City (ECP)
No reviews
Emerald Horizon by Avantstay Beachfront Condo + Resort Pool + Gulf Balcony Views + Near Pier Park & Dining

Emerald Horizon by Avantstay Beachfront Condo + Resort Pool + Gulf Balcony Views + Near Pier Park & Dining

4 out of 5
Save 100% on your flight
Price was $2,163, price is now $1,669 per person
$1,669
per person
Jun 22 - Jun 25
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Panama City (ECP)
No reviews
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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

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
$58 nightly
The price is $65 total per night from Apr 14 to Apr 15
$65 total
Apr 14 - Apr 15
Total with taxes and fees
8/10 Very Good! (2,352 reviews)
My kids loved the pool and easy access to the beach. The view from the balcony was picture perfect. The carpet was not torn but was out dated. The room was clean however the air was left off so we first got there it was a musky smell but after the air conditioner ran a few minutes it disappeared ...

Reviewed on Apr 13, 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 15 to Apr 16
$69 total
Apr 15 - Apr 16
Total with taxes and fees
7.2/10 Good! (1,528 reviews)
The photographs on this site are very deceiving! This hotel is extremely old. The water would not drain out of the shower. It took three flushes to get the toilet empty. Outlets did not work. They doors are cracked and peeling. I did not feel very safe with my two young daughters. There is no wheelchair ...

Reviewed on Apr 13, 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
$139 nightly
The price is $158 total per night from Apr 19 to Apr 20
$158 total
Apr 19 - Apr 20
Total with taxes and fees
8.8/10 Excellent! (2,549 reviews)
Wonderful place to stay! Great breakfast options, perfect location and truly just an amazing experience! Will be back!!

Reviewed on Apr 12, 2026

Hampton Inn & Suites Panama City Beach-Beachfront
See all 7,824 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 $1,027 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.