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.
DoubleTree by Hilton Hotel Tallahassee

DoubleTree by Hilton Hotel Tallahassee

4 out of 5
Capitol Hill
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tallahassee (TLH)
7.6/10 Good! (1,009 reviews)
Walked to Harry’s - our favorite restaurant in the area. Did not like $34 for parking - would have nice to know. That increased our room rate by 30%

Reviewed on Aug. 14, 2025

Pelican Roost E

Pelican Roost E

2 out of 5
per person
Sep 16 - Sep 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
No reviews
Beach House - In Good Company by PHG

Beach House - In Good Company by PHG

3.5 out of 5
per person
Sep 16 - Sep 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
No reviews
BOB Hotels Tallahassee - Boutique on Budget

BOB Hotels Tallahassee - Boutique on Budget

3 out of 5
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tallahassee (TLH)
9/10 Wonderful! (1,314 reviews)
Easy check in. Friendly front desk staff. Room was clean and comfortable.

Reviewed on Aug. 16, 2025

Flamingo Dunes

Flamingo Dunes

4 out of 5
per person
Sep 16 - Sep 21
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Panama City (ECP)
No reviews

Ready to book your vacation to Chipley?

 

Choose your dates

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 $67 per night from Aug 18 to Aug 19
CA $67
CA $99 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (1,743 reviews)
"Great location ,on the beach ,easy to dining and shopping."

Reviewed on Aug. 15, 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 19 to Aug 20
CA $91
CA $132 total
Aug 19 - Aug 20
includes taxes & fees
7/10 Good! (2,309 reviews)
"Great"

Reviewed on Aug. 12, 2025

Radisson Beachfront Hotel - Panama City Beach
Seahaven Beach Hotel

Seahaven Beach Hotel

2 out of 5
15285 Front Beach Rd, Panama City Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Aug 17 to Aug 18
CA $96
CA $118 total
Aug 17 - Aug 18
includes taxes & fees
6/10 (1,837 reviews)
"Everything was great but we had leave day early because my Sister died!"

Reviewed on Aug. 10, 2025

Seahaven Beach Hotel
See all 7,823 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Chipley vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,449 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.