Chipley Vacation Packages

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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!

Top Chipley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sea Shadows 7

Sea Shadows 7

3.5 out of 5
Seacrest
Price was CA $1,890, price is now CA $1,504 per person
CA $1,504
per person
Oct 15 - Oct 19
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
8.6/10 Excellent! (4 reviews)
The property was okay. The views and beach access was great but this property needs some attention. We had a couple minor issues but the property management were very attentive and helpful which was appreciated. The first floor patio furniture was terrible. The corners of the square metal table were completely rusted through and the chairs had rust stains running down them and the round outdoor table was broken within itself, all should be thrown away. It’s a nice property, but needs some TLC.

Reviewed on Mar. 27, 2025

WaterSound Inn

WaterSound Inn

4 out of 5
WaterSound Beach
Price was CA $2,988, price is now CA $2,229 per person
CA $2,229
per person
Oct 15 - Oct 19
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
9.4/10 Exceptional! (93 reviews)
It’s a beautiful option in a beautiful area

Reviewed on Dec. 13, 2024

Walk to the Beach, Pool, 5bdr, 3 Porches Beach Sea-ker's Retreat by Avantstay

Walk to the Beach, Pool, 5bdr, 3 Porches Beach Sea-ker's Retreat by Avantstay

3 out of 5
Price was CA $3,531, price is now CA $2,753 per person
CA $2,753
per person
Oct 15 - Oct 19
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
No reviews
30A Beach House w/ Private Pool, Fire Pit, BBQ & Golf Cart to Rosemary Beach

30A Beach House w/ Private Pool, Fire Pit, BBQ & Golf Cart to Rosemary Beach

3 out of 5
Seacrest
Price was CA $2,713, price is now CA $2,166 per person
CA $2,166
per person
Oct 15 - Oct 19
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
No reviews
Bella Bonita by Avantstay Pool, Peloton & Bikes, Golf Cart, Bonfires

Bella Bonita by Avantstay Pool, Peloton & Bikes, Golf Cart, Bonfires

3 out of 5
Price was CA $2,391, price is now CA $1,942 per person
CA $1,942
per person
Oct 15 - Oct 19
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
No reviews

Ready to book your vacation to Chipley?

 

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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
The price is CA $61 per night from Aug 25 to Aug 26
CA $61
CA $92 total
Aug 25 - Aug 26
includes taxes & fees
7.8/10 Good! (1,775 reviews)
"I loved my stay at the Palmetto!! Great location very clean friendly staff. I already have another reservation for this weekend ro bring my kids. Awesome place to stay."

Reviewed on Aug. 21, 2025

Palmetto Beachfront Hotel, a By the Sea Resort
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
The price is CA $91 per night from Aug 27 to Aug 28
CA $91
CA $132 total
Aug 27 - Aug 28
includes taxes & fees
7/10 Good! (2,329 reviews)
"I love everything about this property"

Reviewed on Aug. 21, 2025

Radisson Beachfront Hotel - Panama City Beach
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
The price is CA $164 per night from Sep 1 to Sep 2
CA $164
CA $186 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,895 reviews)
"CONVENIENT AND WALKABLE TO THE OCEAN SAND. MY FAMILY AND I ARE READY TO COME BACK!"

Reviewed on Aug. 21, 2025

Hampton Inn & Suites Panama City Beach-Beachfront
See all 7,815 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Chipley vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,504 on Expedia. But how much your vacation to Chipley costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chipley?
February, April and September are the best times to search for cheap Chipley vacation packages. Choosing to travel in quieter months means you'll typically find better prices on accommodations and flights.
How many days is enough for Chipley?
The ideal length of your Chipley vacation depends on what you'd like to see. Generally, a few days to a week will give you time to visit all the major sights and discover some hidden spots along the way.
How to find the best Chipley package deals?
Use Expedia's filter tool to help you find some unbeatable Chipley package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Chipley package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Chipley vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Chipley vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Chipley?
If you're planning a spur-of-the-moment Chipley getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Chipley?

  1. Choose your travel dates: What you want to do in Chipley and your favourite season can help you decide when to go.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Chipley. Then, select a property that suits your budget, whether that's a wallet-friendly stay or a more luxurious getaway.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to experience in Chipley. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the ideal Chipley vacation package for you.

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