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

Chipley Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chipley holiday rentals

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, (5 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is AU$338
includes taxes & fees
23 July - 24 July
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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 AU$261
includes taxes & fees
17 Aug - 18 Aug
Cozy Lakefront Airstream

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
The price is AU$268
includes taxes & fees
22 July - 23 July
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

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, (183 reviews)
"We enjoyed our stay. The condo was a goos size and had a nice layout! Beautiful view of the gulf without all the noise!"
United States
Jacob
The price is AU$933
includes taxes & fees
21 Aug - 22 Aug
Calypso Beach Resort by Panhandle Getaways

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,194 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
The price is AU$368
includes taxes & fees
17 Aug - 18 Aug
Origin At Seahaven

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, (31 reviews)
"Super clean and quiet. My cat was welcome to join us. The owner was easy to contact."
United States
Sharon
The price is AU$371
includes taxes & fees
22 July - 23 July
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, we really enjoyed our trip and stay!"
United States
Brent
The price is AU$916
includes taxes & fees
13 Aug - 14 Aug
Calypso Beach Resort Tower 1

Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.0 out of 10, Wonderful, (30 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is AU$952
includes taxes & fees
2 Aug - 3 Aug
Calypso Tower 3 by Panhandle Getaways

Calypso Resort and Towers by Book That Condo

Calypso Resort and Towers by Book That Condo
4.0 star property
Panama City Beach
9.4 out of 10, Exceptional, (8 reviews)
"Perfect location"
United States
Weylin
The price is AU$1,282
includes taxes & fees
29 July - 30 July
Calypso Resort and Towers by Book That Condo

Beach House - The Sanderling by PHG

Beach House - The Sanderling by PHG
4.0 star property
Sunnyside
Beach House - The Sanderling by PHG

Private Pool, Walk to Beach 🏖️, Bright Sun Room, Quiet West End

Private Pool, Walk to Beach 🏖️, Bright Sun Room, Quiet West End
Sunnyside
9.6 out of 10, Exceptional, (128 reviews)
"Nice clean house close to the beach. "
United States
Eric M.
The price is AU$651
includes taxes & fees
26 July - 27 July
Private Pool, Walk to Beach 🏖️, Bright Sun Room, Quiet West End

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, (23 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

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
The price is AU$944
includes taxes & fees
9 Aug - 10 Aug
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

Tidewater Beach Resort by Panhandle Getaways

Tidewater Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
7.4 out of 10, Good, (188 reviews)
"My family and I absolutely loved it! The service was excellent, and the staff were very kind, friendly, and always helpful. From the moment you walk into the apartment, you can immediately notice how clean and well-organized everything is. The smell of cleanliness is very pleasant. The towels, bed linens, and the entire place were spotless and very well maintained. We stayed in apartment 310 on the 30th floor, and the view was absolutely spectacular. The location is also perfect—very central...
United States
Claudia
The price is AU$822
includes taxes & fees
2 Aug - 3 Aug
Tidewater Beach Resort by Panhandle Getaways

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, (257 reviews)
The price is AU$460
includes taxes & fees
2 Aug - 3 Aug
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Gulf Front~Balcony~Fitness Room~2BR Tropic Winds 1104

Gulf Front~Balcony~Fitness Room~2BR Tropic Winds 1104
Panama City Beach
9.2 out of 10, Wonderful, (108 reviews)
"Unbelievable view, loved sitting on the balcony watching the waves and dolphins swim by. Quiet area of the beach which was perfect for us. Bed was comfortable, heat and a/c both worked well (there was a cold snap for part of our trip). Elevators were always available. The other reviews are real as far as parking- I wouldn’t want to try to park a large truck or SUV in the garage. We will definitely stay again next time we are in PCB. "
United States
Kathleen G.
Gulf Front~Balcony~Fitness Room~2BR Tropic Winds 1104

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

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
The price is AU$689
includes taxes & fees
25 July - 26 July
3BR Canal-front Home w/ Wifi & Boat Dock

On the Beach, Best Resort in PCB,Family Friendly,8 Floor, Beach Chairs Included

On the Beach, Best Resort in PCB,Family Friendly,8 Floor, Beach Chairs Included
Panama City Beach
9.2 out of 10, Wonderful, (326 reviews)
"Condo was such a fun experience for our family! Great location and easy access to everything we wanted to do! "
United States
Jennifer F.
The price is AU$577
includes taxes & fees
23 July - 24 July
On the Beach, Best Resort in PCB,Family Friendly,8 Floor, Beach Chairs Included

Grand Panama Beach Resort by Book That Condo

Grand Panama Beach Resort by Book That Condo
4.0 star property
Panama City Beach
9.0 out of 10, Wonderful, (44 reviews)
"The cleanest place we have ever stayed. The condo was perfect. And the view from the balcony was breath taking."
United States
Heather
The price is AU$893
includes taxes & fees
15 Aug - 16 Aug
Grand Panama Beach Resort by Book That Condo

Pelican's Nest - The Hideaway in Panama City

Pelican's Nest - The Hideaway in Panama City
Panama City
9.8 out of 10, Exceptional, (16 reviews)
"Great!"
United States
Richard
Pelican's Nest - The Hideaway in Panama City
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favourite 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 depend 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 AU$368 per night. Entering your travel dates in the search wizard might find you 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?

Elizabeth's Memories - Beach Front: This holiday home rental outside of Chipley is located on the beach, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, an oven and a microwave, 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.