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.
$223 nightly
The price is $243
Aug 16 - Aug 17
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
Aug 17 - Aug 18
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.
$138 nightly
The price is $150
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, (32 reviews)
"We had a wonderful time. The cabin is beautiful and well stocked with all the things you need. The host was great with her communication and always answered promptly. Would definitely stay again and recommend. "
United States
Eva J.
$245 nightly
The price is $261
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
$396 nightly
The price is $421
Aug 17 - Aug 18
Total with taxes and fees
Comfortable Family Retreat in Panama City

6. 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 16 - Aug 17
Total with taxes and fees
3BR Canal-front Home w/ Wifi & Boat Dock

7. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (3 reviews)
"Goo"
United States
Mario
$509 nightly
The price is $576
Aug 17 - Aug 18
Total with taxes and fees
Calypso Beach Resort Tower 1

8. ~ 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.
$383 nightly
The price is $427
Aug 31 - Sep 1
Total with taxes and fees
~ La Conchita ~ w private pool & Firepit

9. 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, (188 reviews)
"Great summer vacation choice!"
United States
Christina
$553 nightly
The price is $626
Sep 15 - Sep 16
Total with taxes and fees
Calypso Beach Resort by Panhandle Getaways

10. Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,201 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
$214 nightly
The price is $242
Aug 26 - Aug 27
Total with taxes and fees
Origin At Seahaven

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, (16 reviews)
"Love the family vibes."
United States
Ashley
$447 nightly
The price is $492
Aug 21 - Aug 22
Total with taxes and fees
Splash Beach Resort by Book That Condo

12. 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.
$243 nightly
The price is $271
Aug 24 - Aug 25
Total with taxes and fees
Studio Home Just a Minute Walk from the Beach! Book before gone!

13. 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, (36 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
$554 nightly
The price is $627
Aug 18 - Aug 19
Total with taxes and fees
Calypso Tower 3 by Panhandle Getaways

14. 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, (26 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
$350 nightly
The price is $380
Aug 16 - Aug 17
Total with taxes and fees
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

15. 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 24 - Aug 25
Total with taxes and fees
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

16. 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, (260 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
$270 nightly
The price is $300
Aug 16 - Aug 17
Total with taxes and fees
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

17. Origin 1333 - Studio - Amazing Value - Gulf Views

Origin 1333 - Studio - Amazing Value - Gulf Views
Panama City Beach
9.4 out of 10, Exceptional, (55 reviews)
"Great location and amenities. "
United States
Brian W.
$271 nightly
The price is $302
Aug 18 - Aug 19
Total with taxes and fees
Origin 1333 - Studio - Amazing Value - Gulf Views

18. Beach Service and FREE Activities! 5th Floor! Summer Deals!

Beach Service and FREE Activities! 5th Floor! Summer Deals!
Panama City Beach
9.2 out of 10, Wonderful, (164 reviews)
"Loved that this unit was so spacious and the king beds in both bedrooms. "
United States
frank r.
Beach Service and FREE Activities! 5th Floor! Summer Deals!

19. Aqua Beach Resort by Panhandle Getaways

Aqua Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
Justin
Aqua Beach Resort by Panhandle Getaways

20. Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park

Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park
Panama City Beach
9.6 out of 10, Exceptional, (27 reviews)
"The room was very clean and well taken care of! Would stay there again!"
United States
Kiley S.
$393 nightly
The price is $438
Aug 17 - Aug 18
Total with taxes and fees
Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park
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 $242 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.

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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 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 6 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.