A waterfall cascading over a rocky cliff surrounded by lush green ferns and foliage.

Chipley Vacation Rentals

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Our top choices for Chipley vacation 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.
$220 nightly
The price is $240
Sep 2 - Sep 3
Total with taxes and fees
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.
$153 nightly
The price is $166
Sep 2 - Sep 3
Total with taxes and fees
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.
$135 nightly
The price is $147
Sep 8 - Sep 9
Total with taxes and fees
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.
$246 nightly
The price is $262
Sep 7 - Sep 8
Total with taxes and fees
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
$553 nightly
The price is $626
Sep 2 - Sep 3
Total with taxes and fees
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
$498 nightly
The price is $564
Sep 10 - Sep 11
Total with taxes and fees
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.
$334 nightly
The price is $372
Oct 1 - Oct 2
Total with taxes and fees
~ 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
$520 nightly
The price is $588
Sep 3 - Sep 4
Total with taxes and fees
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.
$271 nightly
The price is $302
Sep 2 - Sep 3
Total with taxes and fees
Private - Waterfront Cottage - Panama City, FL

10. Octa Collection on Front Beach

Octa Collection on Front Beach
4.0 star property
Long Beach
$321 nightly
The price is $364
Sep 4 - Sep 5
Total with taxes and fees
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
$451 nightly
The price is $496
Sep 9 - Sep 10
Total with taxes and fees
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.
$565 nightly
The price is $630
Sep 2 - Sep 3
Total with taxes and fees
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.
$319 nightly
The price is $356
Sep 2 - Sep 3
Total with taxes and fees
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.
$264 nightly
The price is $294
Sep 6 - Sep 7
Total with taxes and fees
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
$490 nightly
The price is $554
Sep 2 - Sep 3
Total with taxes and fees
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
$339 nightly
The price is $368
Sep 2 - Sep 3
Total with taxes and fees
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
$1,406 nightly
The price is $1,575
Sep 2 - Sep 3
Total with taxes and fees
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.
$254 nightly
The price is $283
Sep 2 - Sep 3
Total with taxes and fees
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.
$674 nightly
The price is $751
Sep 2 - Sep 3
Total with taxes and fees
🏝️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.
$473 nightly
The price is $527
Sep 9 - Sep 10
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chipley vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chipley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $456 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chipley?

Yes, there are vacation rentals close to popular points of interest in Chipley, or you can go with a secluded option if you'd like a relaxing place to 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's the top vacation rental that Chipley has to offer?

Tidal Charm by AvantStay | Walk to Beach, Community Pool, Balcony, Ocean Views: Visitors like this Chipley vacation home rental. It is located near the beach and has a balcony, a selection of games, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in Chipley?

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

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 vacation rentals like in Chipley?

Vacation rentals are private accommodations you can book for a couple days or more in Chipley. Vacation rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.