
Chipley Vacations from $1,656
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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.

Emerald Horizon by Avantstay Beachfront Condo + Resort Pool + Gulf Balcony Views + Near Pier Park & Dining
Save 100% on your flight
Price was $2,237, price is now $1,656 per person
$1,656
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Panama City (ECP)
No reviews

Steps to Private Beach Access Pool + Bikes Seacrest 30A
Rosemary Beach
Save 100% on your flight
Price was $3,657, price is now $2,638 per person
$2,638
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Panama City (ECP)
10/10 Exceptional! (1 review)
This house is well maintained and clean with comfortable beds and plenty of space for our family of five. There is definitely room for more people too. Each room has its own bathroom which makes getting ready for outings much easier. The house is located in the seacrest beach section of Rosemary Beach and is only a five minute walk to pool and 10 minute walk to beach. The pool lagoon area is beautiful with a cafe and bathrooms and plenty of seating for the month of August. The beach has a beautiful entrance and white sand with clear waters and chair/umbrellas to rent for the day. There is also a very good cafe steps up from beach called Crabby Steve’s high point. We walked everywhere in seacrest and proper Rosemary beach near the Pearl Hotel. We ate good meals every day. Lots of restaurants to try. This house did not have bikes included in our rental price. If this is important to you check out bike rental options before you go. Our family swam in pool and golf most of day, especially bc August weather brings so much heat and humidity to this area, and we got dressed nicely and walked to dinner in the evening and then walked to ice cream and shops before going back to house. We had quiet, quality family time.
Reviewed on Aug 27, 2025

Sandy Pelican by Avantstay Exclusive Beach Access + Private Pool + Firepit + Balcony Sunset Views
Seacrest
Save 100% on your flight
Price was $4,333, price is now $3,131 per person
$3,131
per person
Jul 23 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Panama City (ECP)
No reviews

The Pearl Hotel
Rosemary Beach
Save 100% on your flight
Price was $2,811, price is now $2,073 per person
$2,073
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Panama City (ECP)
9.6/10 Exceptional! (218 reviews)
This hotel was absolutely beautiful. Well worth the money
Reviewed on Apr 16, 2026

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.
Chipley Hotel Deals

Palmetto Beachfront Hotel, a By the Sea Resort
17255 Front Beach Road Panama City Beach FL
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $70 total per night from May 10 to May 11
$70 total
May 10 - May 11
Total with taxes and fees
7.8/10 Good! (2,455 reviews)
Clean and quite with great view of the beach.
Reviewed on May 7, 2026

Radisson Beachfront Hotel - Panama City Beach
15325 Front Beach Road Panama City Beach FL
Fully refundable
$98 nightly
The price is $111 total per night from May 10 to May 11
$111 total
May 10 - May 11
Total with taxes and fees
7/10 Good! (2,672 reviews)
The view was great but the rooms need to be updated the bed was awful we had to switch rooms the next night because of it
Reviewed on May 8, 2026

Chateau Beachfront Hotel, A By The Sea Resort
12525 Front Beach Rd Panama City Beach FL
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $70 total per night from May 10 to May 11
$70 total
May 10 - May 11
Total with taxes and fees
7/10 Good! (1,632 reviews)
Clean, easy access for shopping and restaurants, friendly staff, beautiful oceanview front.
Reviewed on May 7, 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 |
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