Chipley Vacations from $1,209

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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.
The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,725, price is now $1,209 per person
$1,209
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
9.4/10 Exceptional! (184 reviews)
Nice and clean room (#308), but I thought the room was configured oddly because the bed blocks the door to the balcony. I would have positioned the bed the other way around (but that's just me). Staff are very attentive and seem to enjoy and happy with their job. Although our room was facing the main street, it was very quiet. The beach is perfect for swimming, very calm/very small waves and clear water.

Reviewed on Oct 14, 2025

WaterSound Inn

WaterSound Inn

4 out of 5
WaterSound Beach
Save 100% on your flight
Price was $1,834, price is now $1,272 per person
$1,272
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
9.4/10 Exceptional! (95 reviews)
It’s a beautiful option in a beautiful area

Reviewed on Dec 13, 2024

Beach Bike Cottage by Avantstay Walk to Beach, Resort Pool

Beach Bike Cottage by Avantstay Walk to Beach, Resort Pool

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $3,619, price is now $2,829 per person
$2,829
per person
Dec 28 - Jan 1
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Panama City (ECP)
No reviews
Beachfront Breeze by Avantstay Beachfront Condo

Beachfront Breeze by Avantstay Beachfront Condo

3 out of 5
Lower Grand Lagoon
Save 100% on your flight
Price was $1,627, price is now $1,272 per person
$1,272
per person
Dec 20 - Dec 27
found 6 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Panama City (ECP)
No reviews
Dunn Inn 2 by Avantstay Walk to Beach, Pool Access, Sleeps 17!

Dunn Inn 2 by Avantstay Walk to Beach, Pool Access, Sleeps 17!

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $3,098, price is now $2,443 per person
$2,443
per person
Dec 28 - Jan 1
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Panama City (ECP)
No reviews
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Discover the most popular places to visit in Chipley

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

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
$55 nightly
The price is $62 total per night from Dec 5 to Dec 6
$62 total
Dec 5 - Dec 6
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
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
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 17 to Nov 18
$118 total
Nov 17 - Nov 18
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 7,788 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 $1,209 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.