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Chipley Holiday Rentals

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Our top choices for Chipley holiday rentals

1. Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
10.0 out of 10, Exceptional, (6 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is NZ$404
includes taxes & fees
1 Sept - 2 Sept
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

2. Cozy Lakefront Airstream

Cozy Lakefront Airstream
Chipley
9.8 out of 10, Exceptional, (14 reviews)
"We loved the property, enjoyed all the amenities and relaxed comfortably."
United States
Lesley H.
The price is NZ$281
includes taxes & fees
1 Sept - 2 Sept
Cozy Lakefront Airstream

3. Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Chipley
10.0 out of 10, Exceptional, (1 review)
"Very nice place to stay. Host was very helpful and accommodating. Enjoyed being way out in the country."
United States
Gwen S.
The price is NZ$249
includes taxes & fees
1 Sept - 2 Sept
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

4. Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.8 out of 10, Exceptional, (35 reviews)
"Amazing place"
United States
Alex R.
The price is NZ$438
includes taxes & fees
7 Sept - 8 Sept
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

5. Calypso Beach Resort Tower 2 by Panhandle Getaways

Calypso Beach Resort Tower 2 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (191 reviews)
"Great summer vacation choice!"
United States
Christina
The price is NZ$1,050
includes taxes & fees
1 Sept - 2 Sept
Calypso Beach Resort Tower 2 by Panhandle Getaways

6. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.0 out of 10, Wonderful, (7 reviews)
"The decor was nice and the rooms were clean also had a great view of the Gulf"
United States
Elijah
The price is NZ$1,057
includes taxes & fees
3 Sept - 4 Sept
Calypso Beach Resort Tower 1

7. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (55 reviews)
"Great location!Kids loved the pool even if it was cold. The owners were amazing, and quick to respond."
United States
Ellen D.
The price is NZ$731
includes taxes & fees
29 Sept - 30 Sept
~ La Conchita ~ w private pool & Firepit

8. Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (37 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is NZ$1,005
includes taxes & fees
1 Sept - 2 Sept
Calypso Tower 3 by Panhandle Getaways

9. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (19 reviews)
"Perfect stay "
United States
Jess C.
The price is NZ$534
includes taxes & fees
28 Sept - 29 Sept
Private - Waterfront Cottage - Panama City, FL

10. Octa Collection on Front Beach

Octa Collection on Front Beach
4.0 star property
Long Beach
The price is NZ$555
includes taxes & fees
10 Sept - 11 Sept
Octa Collection on Front Beach

11. Splash Beach Resort by Book That Condo

Splash Beach Resort by Book That Condo
4.0 star property
Panama City Beach
9.4 out of 10, Exceptional, (17 reviews)
"The location, amenities, and room were clean and spacious. Elevators were quick and available."
United States
Ben
The price is NZ$826
includes taxes & fees
9 Sept - 10 Sept
Splash Beach Resort by Book That Condo

12. Corner Condo - Stunning Gulf Views -Comp. Beach Service, Water Park & Lazy River

Corner Condo - Stunning Gulf Views -Comp. Beach Service, Water Park & Lazy River
Panama City Beach
9.8 out of 10, Exceptional, (229 reviews)
"If you are looking for a beautifully decorated condo, right on the beach, that is close to the “strip” to get some really good meals quickly but far enough away that it is still quiet, this is the perfect place!! The kitchen is stocked well with everything we needed for our stay and the beds were comfortable and we loved that there were so many extra pillows! I really like that there was a broom available for cleaning up the sand. The resort was very clean and safe. The courtesy patrol was on...
United States
jessica t.
Corner Condo - Stunning Gulf Views -Comp. Beach Service, Water Park & Lazy River

13. Celadon 15th private parking + Beach Chair Service!

Celadon 15th private parking + Beach Chair Service!
Panama City Beach
10.0 out of 10, Exceptional, (180 reviews)
"We absolutely had the best vacation at PCB. "
United States
Tracy D.
The price is NZ$585
includes taxes & fees
1 Sept - 2 Sept
Celadon 15th private parking + Beach Chair Service!

14. Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
Panama City Beach
9.4 out of 10, Exceptional, (262 reviews)
"Nice stay"
United States
Dana M.
The price is NZ$492
includes taxes & fees
1 Sept - 2 Sept
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

15. Grand Panama Beach Resort by Panhandle Getaways

Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.4 out of 10, Very good, (118 reviews)
"Great view and helpful staff."
United States
Terri
The price is NZ$930
includes taxes & fees
1 Sept - 2 Sept
Grand Panama Beach Resort by Panhandle Getaways

16. Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
Laguna Beach
8.8 out of 10, Excellent, (27 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is NZ$603
includes taxes & fees
1 Sept - 2 Sept
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

17. Beach House - The Sandcastle by PHG

Beach House - The Sandcastle by PHG
4.0 star property
Laguna Beach
The price is NZ$2,677
includes taxes & fees
1 Sept - 2 Sept
Beach House - The Sandcastle by PHG

18. Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!

Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!
Panama City Beach
9.8 out of 10, Exceptional, (164 reviews)
"We had a great time! The view was great and the place was very clean! "
United States
Chloe G.
The price is NZ$473
includes taxes & fees
1 Sept - 2 Sept
Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!

19. 🏝️Luxury Ocean Front 22nd Floor. HUGE Balcony, Amazing Views. FREE Beach Service!

🏝️Luxury Ocean Front 22nd Floor. HUGE Balcony, Amazing Views. FREE Beach Service!
Panama City Beach
10.0 out of 10, Exceptional, (194 reviews)
"We loved this condo. In a perfect location on the beach; far enough away to be peaceful/less crowded but close enough to everything if you decide to go in. The condo is very well kept with great amenities and decor. We will definitely be booking this in the future!"
United States
Michael C.
The price is NZ$1,247
includes taxes & fees
2 Sept - 3 Sept
🏝️Luxury Ocean Front 22nd Floor. HUGE Balcony, Amazing Views. FREE Beach Service!

20. Oceanfront Luxury 6th Floor Splash Resort: 2BR/2BA King Unit, Free Beach Service

Oceanfront Luxury 6th Floor Splash Resort: 2BR/2BA King Unit, Free Beach Service
Panama City Beach
9.0 out of 10, Wonderful, (137 reviews)
"Great place to stay"
United States
Josh G.
The price is NZ$883
includes taxes & fees
5 Sept - 6 Sept
Oceanfront Luxury 6th Floor Splash Resort: 2BR/2BA King Unit, Free Beach Service
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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Top Chipley Hotel Reviews

Find out more about Chipley

Everything you need to know about Chipley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chipley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chipley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chipley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chipley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley holiday rentals we have selected for you start as low as NZ$761 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chipley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chipley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chipley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chipley?

Yes, there are holiday rentals close to the most popular sights in Chipley, or you can select a more secluded option if you're looking for a relaxing stay. Chipley is known for its churches and lake views. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Chipley has to offer?

Tidal Charm by AvantStay | Walk to Beach, Community Pool, Balcony, Ocean Views: This holiday home rental outside of Chipley is located near the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchenette with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chipley?

Choose from 7 Expedia holiday rentals in Chipley for a memorable holiday.

What can I see and do in Chipley?

Falling Waters State Park and Lucas Lake are a couple of lovely local spots to get outside and enjoy nature. Pal's Park and River Lake are other places to visit while you're in town.

What are holiday rentals like in Chipley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chipley. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.