Chipley Vacations from $349

Book a Hotel + Flight or Car together to unlock savings

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.
Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

2.5 out of 5
Price was $493, price is now $349 per person
$349
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
14.4/10 Exceptional! (1,255 reviews)
Check in staff was friendly, the room had a kitchen (with dishes and cutlery which was appreciated!). The room was very clean however we discovered one set of sheets were soiled when going to bed. It was after midnight and the staff brought us clean sheets and then in the morning made it up to us for our troubles. Had a great stay, loved the wonderful view and would happily stay again.

Reviewed on Nov 17, 2025

Margaritaville Beach Cottage Resort PCB

Margaritaville Beach Cottage Resort PCB

4.5 out of 5
Save 100% on your flight
Price was $1,457, price is now $938 per person
$938
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
18.8/10 Exceptional! (10 reviews)
The property itself is amazing. Both the pool/amenities & house was beautiful and clean. Unfortunately the on premise service does not meet the same standard. Check in was 4:00, which is on the later side. We arrived at 2:00pm and the said they would text us if our room was ready early. 4:00pm hit and no call so I went back to the front desk to check in and I was told my room was still not ready. Long story short, we finally got in at 4:45, so day one was pretty shot… if you are planning on a short trip (say a couple nights) I could not recommend this place due to the check in issues. On Friday night I went to the restaurant at 5:30 for dinner. We waited at the hostess stand for 10 minutes to just wait - no one came. No staff to serve dinner…? We had no choice but to get in our car and drive somewhere… On Saturday afternoon we decided to head over to the pool bar and watch college football. We headed over at 4pm and the bar already closed for the day! 4pm on a Saturday - pool bar closed… There is another bar just outside the pool that’s connected to the restaurant (the one no one served us the night before). We decided to try it again. We asked them to turn on the TN football game. It took them 20-30 minutes to try. Once they tried, they flips through a few screens and said, “sorry, we don’t have it.” We left, walked to our room, and watched the game inside our room… In summary - beautiful place, very clean, but non existent guest service.

Reviewed on Oct 12, 2025

WaterSound Inn

WaterSound Inn

4 out of 5
WaterSound Beach
Save 100% on your flight
Price was $1,793, price is now $1,181 per person
$1,181
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
18.8/10 Exceptional! (95 reviews)
It’s a beautiful option in a beautiful area

Reviewed on Dec 13, 2024

The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,577, price is now $1,751 per person
$1,751
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
18.8/10 Exceptional! (188 reviews)
Loved our stay the kind staff and clean rooms and the views and surrounding amenities!

Reviewed on Nov 19, 2025

Sandpiper Beacon Beach Resort

Sandpiper Beacon Beach Resort

3 out of 5
Price was $508, price is now $370 per person
$370
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
16/10 Exceptional! (394 reviews)
This place was perfect for a family!

Reviewed on Oct 28, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chipley
View all trips

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

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
$79 nightly
The price is $90 total per night from Nov 30 to Dec 1
$90 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (2,141 reviews)
THE VIEW WAS BREATH TAKING!

Reviewed on Nov 14, 2025

Hampton Inn & Suites Panama City Beach-Beachfront
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
$49 nightly
The price is $56 total per night from Nov 20 to Nov 21
$56 total
Nov 20 - Nov 21
Total with taxes and fees
7/10 Good! (1,256 reviews)
Pool was warm, but not as warm as I remembered from last February! Clean room, nice staff with ease of check in

Reviewed on Nov 13, 2025

Chateau Beachfront Hotel, A By The Sea Resort
Hyatt Place Panama City Beach

Hyatt Place Panama City Beach

3 out of 5
15727 FRONT BEACH ROAD Panama City Beach FL
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Nov 20 to Nov 21
$118 total
Nov 20 - Nov 21
Total with taxes and fees
9.2/10 Wonderful! (1,383 reviews)
Place was fantastic and we will be going back. Room is spacious with full size frig and microwave. Best shower water pressure I've ever had. Location convenient to Pier Park and the beach view was wonderful. Breakfast was fantastic. Hot tub was hot. Lazy River would be fun for the family. Room was ...

Reviewed on Nov 13, 2025

Hyatt Place Panama City Beach
See all 7,800 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chipley vacation package cost?
You'll find cheap prices from $349 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

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