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. 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.
$141 nightly
The price is $153
Aug 11 - Aug 12
Total with taxes and fees
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

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
Aug 17 - Aug 18
Total with taxes and fees
Cozy Lakefront Airstream

3. 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
Aug 9 - Aug 10
Total with taxes and fees
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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, (32 reviews)
"Super clean and quiet. My cat was welcome to join us. The owner was easy to contact."
United States
Sharon
$246 nightly
The price is $262
Aug 20 - Aug 21
Total with taxes and fees
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

5. Comfortable Family Retreat in Panama City

Comfortable Family Retreat in Panama City
Panama City
$397 nightly
The price is $422
Aug 17 - Aug 18
Total with taxes and fees
Comfortable Family Retreat in Panama City

6. ~ 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.
$398 nightly
The price is $444
Sep 1 - Sep 2
Total with taxes and fees
~ La Conchita ~ w private pool & Firepit

7. 3BR Canal-front Home w/ Wifi & Boat Dock

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
$450 nightly
The price is $482
Aug 9 - Aug 10
Total with taxes and fees
3BR Canal-front Home w/ Wifi & Boat Dock

8. Studio Home Just a Minute Walk from the Beach! Book before gone!

Studio Home Just a Minute Walk from the Beach! Book before gone!
Panama City Beach
9.0 out of 10, Wonderful, (22 reviews)
"Just a nice place to stay while in Pcb."
United States
Benjamin P.
$241 nightly
The price is $269
Aug 26 - Aug 27
Total with taxes and fees
Studio Home Just a Minute Walk from the Beach! Book before gone!

9. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (2 reviews)
"Goo"
United States
Mario
$509 nightly
The price is $576
Aug 13 - Aug 14
Total with taxes and fees
Calypso Beach Resort Tower 1

10. Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis
3.5 star property
Panama City Beach
$528 nightly
The price is $601
Aug 17 - Aug 18
Total with taxes and fees
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

11. Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,197 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
$217 nightly
The price is $246
Aug 14 - Aug 15
Total with taxes and fees
Origin At Seahaven

12. Gulf Front Retreat with King Bed and Pool

Gulf Front Retreat with King Bed and Pool
Laguna Beach
9.8 out of 10, Exceptional, (31 reviews)
"Great stay! Peaceful and quiet location, but close to everything."
United States
Rachel M.
$353 nightly
The price is $390
Aug 9 - Aug 10
Total with taxes and fees
Gulf Front Retreat with King Bed and Pool

13. Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!

Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!
Panama City Beach
9.2 out of 10, Wonderful, (27 reviews)
"Everything was great!! The location was awesome!! We had a great time!!!"
United States
Jason W.
Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!

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, (258 reviews)
"Every thing was what we saw in the advertisement. We would rent again."
United States
melinda h.
$291 nightly
The price is $325
Aug 9 - Aug 10
Total with taxes and fees
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

15. Calypso Beach Resort by Panhandle Getaways

Calypso Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (186 reviews)
"Great summer vacation choice!"
United States
Christina
$565 nightly
The price is $639
Aug 9 - Aug 10
Total with taxes and fees
Calypso Beach Resort by Panhandle Getaways

16. Origin 0538- Studio - Breath Taking Gulf Views

Origin 0538- Studio - Breath Taking Gulf Views
Panama City Beach
9.2 out of 10, Wonderful, (32 reviews)
"great place to stay, will definately be staying there again"
United States
John L.
$260 nightly
The price is $290
Aug 10 - Aug 11
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views

17. 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, (16 reviews)
"Love the family vibes."
United States
Ashley
$447 nightly
The price is $492
Aug 13 - Aug 14
Total with taxes and fees
Splash Beach Resort by Book That Condo

18. Coastal Breeze Perfect Family Getaway/ Sleep 9

Coastal Breeze Perfect Family Getaway/ Sleep 9
Laguna Beach
9.4 out of 10, Exceptional, (79 reviews)
"Property was easy to find. Very spacious. Plenty of room for our family. Great location in proximity to the beach, food, and shopping."
United States
Brittany K.
$313 nightly
The price is $346
Sep 1 - Sep 2
Total with taxes and fees
Coastal Breeze Perfect Family Getaway/ Sleep 9

19. 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, (34 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
$543 nightly
The price is $614
Aug 9 - Aug 10
Total with taxes and fees
Calypso Tower 3 by Panhandle Getaways

20. Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!
Panama City Beach
9.4 out of 10, Exceptional, (185 reviews)
"Pet friendly. Clean room. "
United States
amanda l.
$534 nightly
The price is $595
Aug 10 - Aug 11
Total with taxes and fees
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!
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 $246 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?

Beach House - Sunset Paradise by PHG: You might want to consider this vacation home rental near Chipley, which is located by the ocean and offers a private balcony, air-conditioning, and Netflix to help you feel perfectly comfortable in your new surroundings. Amenities like a coffee maker and free parking are also available for your convenience.

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.