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.
BOB Hotels Tallahassee - Boutique on Budget
Price was CA $1,433, price is now CA $1,271 per person
CA $1,271
per person
Jun 21 - Jun 28
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tallahassee (TLH)
9/10 Wonderful! (2,182 reviews)
Clean, quiet, safe, comfortable
Reviewed on May 8, 2026
La Familia Stay Inn
Price was CA $3,360, price is now CA $2,710 per person
CA $2,710
per person
Jun 21 - Jun 28
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tallahassee (TLH)
5.6/10 (29 reviews)
Room was clean and staff was super nice. Really enjoyed my stay.
Reviewed on Dec 16, 2025
Staybridge Suites Tallahassee by IHG
Price was CA $1,693, price is now CA $1,431 per person
CA $1,431
per person
Jun 21 - Jun 28
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tallahassee (TLH)
9/10 Wonderful! (1,001 reviews)
Everything was perfect, the problem was with the management, I booked my room in November 2025 for May 2026 for three nights Friday-Monday. When I did the check in I mentioned I wanted to stay only 2 nights. They said it could not be canceled the last night. The
Reviewed on May 7, 2026
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
The price is CA $111 per night from May 18 to May 19
CA $111
CA $149 total
May 18 - May 19
includes taxes & fees
7.8/10 Good! (2,457 reviews)
This was an older motel, but very nice. It had beach front or across the street rooms. The price was great especially across the street
Reviewed on May 8, 2026
Radisson Beachfront Hotel - Panama City Beach
15325 Front Beach Road Panama City Beach FL
Fully refundable
The price is CA $108 per night from May 10 to May 11
CA $108
CA $152 total
May 10 - May 11
includes taxes & fees
7/10 Good! (2,675 reviews)
The view from the balcony was great. The rooms were good size and the kitchenette was good. Apparently Radisson's standards have gone down considerably, although it has been awhile since I stayed at Radisson. Upon arriving I noticed how filthy the floors were. They were a wood laminate or something ...
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
The price is CA $81 per night from May 10 to May 11
CA $81
CA $112 total
May 10 - May 11
includes taxes & fees
7/10 Good! (1,634 reviews)
The pictures lie! There is no pool and the rooms look like something from a scary movie. The hotel is something off of girls gone wild. Don’t do it!
Reviewed on May 8, 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.
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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.
