Chipley Vacations from $537
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.
Sandpiper Beacon Beach Resort
Price was $698, price is now $537 per person
$537
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Panama City (ECP)
8/10 Very Good! (553 reviews)
We stayed at the last minute and had a great beach view. We really didn’t have to leave because it’s like a miniature resort in some ways. Very family and pet friendly. It was clean and had plenty of parking. There are indoor pools and play areas and a nice little boardwalk that you can sit and watch the beach from if you don’t want to go down to the beach. And there’s the bar and karaoke area on the beach side as well. They also have a gift shop with some basic items like clothing and gifts that you would imagine at a place like this. There’s also a little coffee shop. You can walk right across the street and have a nice breakfast at the restaurant.
Reviewed on Jun 9, 2026
DoubleTree by Hilton Hotel Tallahassee
Capitol Hill
Price was $1,198, price is now $917 per person
$917
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Tallahassee (TLH)
7.4/10 Good! (1,003 reviews)
Doubeltree Tally is gorgeous and Brianna was incredibly helpful. The room was clean and had great views of the downtown square. Plenty of shops and restaurants within walking distance. We will definitely be back.
Reviewed on Jun 8, 2026
Sugar Sands Beachfront Hotel, a By The Sea Resort
Laguna Beach Estates
Price was $764, price is now $587 per person
$587
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Panama City (ECP)
7.8/10 Good! (1,002 reviews)
The view was nice the staff was friendly,there was what appears to be mold in the bathroom and spider webs on the wall but over all was ok.
Reviewed on Jun 2, 2026
The Pearl Hotel
Rosemary Beach
Save 100% on your flight
Price was $1,896, price is now $1,460 per person
$1,460
per person
Aug 7 - Aug 10
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Panama City (ECP)
9.4/10 Exceptional! (222 reviews)
The Pearl is a wonderful place to stay! Everything was perfect
Reviewed on May 22, 2026
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.
Chipley Hotel Deals
Radisson Beachfront Hotel - Panama City Beach
15325 Front Beach Road Panama City Beach FL
$189 nightly
The price is $214 total per night from Jun 14 to Jun 15
$214 total
Jun 14 - Jun 15
Total with taxes and fees
7/10 Good! (2,752 reviews)
"I wasn’t able to use my microwave or refrigerator as well as ice bucket due to rust mold and mildew some staff was very disrespectful as I bought my concerns to them also a wash cloth was dirty folded up nice and neat when I opened the washcloth i noticed it stained with dirt also had issues with ..."
Reviewed on Jun 10, 2026
Palmetto Beachfront Hotel, a By the Sea Resort
17255 Front Beach Road Panama City Beach FL
$130 nightly
The price is $146 total per night from Jun 14 to Jun 15
$146 total
Jun 14 - Jun 15
Total with taxes and fees
7.8/10 Good! (2,560 reviews)
"From check in to check out the customer service was extremely wonderful. At the time of check in there was a man who wasn't friendly to the front desk clerk Anthony but that didn't stop Anthony from doing his job or being polite to him or anyone else. Great job Anthony! Wonderful place ill definitely ..."
Reviewed on Jun 10, 2026
Chateau Beachfront Hotel, A By The Sea Resort
12525 Front Beach Rd Panama City Beach FL
$143 nightly
The price is $161 total per night from Jun 11 to Jun 12
$161 total
Jun 11 - Jun 12
Total with taxes and fees
7/10 Good! (1,781 reviews)
"Our room looked nothing like the pictures shown. It was in horrible shape and in need of massive updating and improvements and could have been cleaner. I would not walk barefoot at all during my stay. The toilet was not even stable and sunk every time used. The old floor has many sunken spots throughout ..."
Reviewed on Jun 9, 2026
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
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Falling Waters State Park
- Bonifay Hotels
- Cheap Hotels in Bonifay
- Cabin Rentals in Bonifay
- Pet-Friendly Hotels in Bonifay
- Marriott Hotels & Resorts in Bonifay
- Motels in Bonifay
- Gay friendly Hotels in Bonifay
- Hotels with a Pool in Bonifay
- Resorts & Hotels with Spas in Bonifay
- Wyndham Hotels in Bonifay
- Hotels with Restaurants in Bonifay
- Beach Hotels in Bonifay
- 5 Star Hotels in Bonifay
- 3 Star Hotels in Bonifay
- Family Hotels in Bonifay
- Cottondale Hotels
- B&B in Cottondale
- Cabin Rentals in Cottondale
- Marriott Hotels & Resorts in Cottondale
- Alford Hotels
- B&B in Alford
- 4 Star Hotels in Alford
- Villager Lodge Hotels in Alford
- Wausau Hotels
- Cabin Rentals in Wausau
- 3 Star Hotels in Wausau
- 5 Star Hotels in Wausau
- Jacob City Hotels
- Graceville Hotels
- Vacation Homes in Graceville
- 3 Star Hotels in Graceville
- B&B in Graceville
- 4 Star Hotels in Graceville
- Motels in Graceville
- Cottages in Graceville
- 5 Star Hotels in Graceville
- Rv Parks in Graceville
- Campbellton Hotels
- Motels in Campbellton
- Vernon Hotels
- Caryville Hotels
- 3 Star Hotels in Caryville
- Motels in Caryville
- Sunny Hills Hotels
- Hotels near John Russ House
- Flights from Washington County
- Flights to Bonifay
- Flights from Bonifay
- Flights from Holmes County
- Flights to Cottondale
- Flights from Cottondale
- Flights from Alford
- Flights to Alford
- Flights to Graceville
- Flights from Graceville
- Flights from Campbellton
- Flights to Campbellton
- Flights to Caryville
- Flights from Caryville
- Car rentals near Bonifay
- Island Car Rentals Rental Cars in Bonifay
- Hertz Rental Cars in Bonifay
- Advantage Rent-A-Car Rental Cars in Bonifay
- Enterprise Rental Cars in Bonifay
- Avis Rental Cars in Bonifay
- Standard Car Rentals in Bonifay
- Midsize Car Rentals in Bonifay
- Car rentals near Cottondale
- Car rentals near Alford
- Car rentals near Wausau
- Car rentals near Jacob City
- Car rentals near Graceville
- Enterprise Rental Cars in Graceville
- Ace New Zealand Rental Cars in Graceville
- Car rentals near Campbellton
- Car rentals near Noma
- Car rentals near Vernon
- Car rentals near Esto
- Car rentals near Caryville
- Car rentals near Sunny Hills
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.