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

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
Jul 2 - Jul 3
Total with taxes and fees
Cozy Lakefront Airstream

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.
$226 nightly
The price is $247
Jul 23 - Jul 24
Total with taxes and fees
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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
$173 nightly
The price is $189
Jul 13 - Jul 14
Total with taxes and fees
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
$598 nightly
The price is $677
Jul 31 - Aug 1
Total with taxes and fees
Calypso Beach Resort Tower 1

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
$175 nightly
The price is $186
Jul 5 - Jul 6
Total with taxes and fees
Pelican's Nest - The Hideaway in Panama City

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

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.6 out of 10, Exceptional, (29 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
Jul 19 - Jul 20
Total with taxes and fees
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (14 reviews)
"Perfect stay "
United States
Jess C.
$296 nightly
The price is $330
Jul 6 - Jul 7
Total with taxes and fees
Private - Waterfront Cottage - Panama City, FL

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
$677 nightly
The price is $775
Jul 14 - Jul 15
Total with taxes and fees
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

Walk to Beach + Restaurants: PCB Resort Condo!

Walk to Beach + Restaurants: PCB Resort Condo!
3.0 star property
Panama City Beach
9.0 out of 10, Wonderful, (10 reviews)
"Thank you great experience with my stay."
United States
Vanessa
$303 nightly
The price is $343
Jul 5 - Jul 6
Total with taxes and fees
Walk to Beach + Restaurants: PCB Resort Condo!

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
$382 nightly
The price is $415
Jul 14 - Jul 15
Total with taxes and fees
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

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, (21 reviews)
"Just a nice place to stay while in Pcb."
United States
Benjamin P.
$278 nightly
The price is $310
Jul 12 - Jul 13
Total with taxes and fees
Studio Home Just a Minute Walk from the Beach! Book before gone!

Charming 1-bedroom condo on lovely Panama City Beach

Charming 1-bedroom condo on lovely Panama City Beach
Panama City
9.6 out of 10, Exceptional, (20 reviews)
"perfect for budget trip"
United States
Liam B.
$204 nightly
The price is $227
Jul 12 - Jul 13
Total with taxes and fees
Charming 1-bedroom condo on lovely Panama City Beach

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.
$318 nightly
The price is $355
Jul 6 - Jul 7
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,190 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
$249 nightly
The price is $282
Jul 29 - Jul 30
Total with taxes and fees
Origin At Seahaven

Sterling Breeze by Panhandle Getaways

Sterling Breeze by Panhandle Getaways
3.5 star property
Panama City Beach
8.4 out of 10, Very Good, (34 reviews)
"Not clean , had a water leak in the kitchen they fixed next day. No internet or WF that all, need your own WF or hotspot. Only 2 elevators in the building, pool it was ok but nothing else was offered that ice cream. For someone who called this resort …. Not resort they all. Just regular apartment building!"
United States
Slavica
$524 nightly
The price is $593
Jul 17 - Jul 18
Total with taxes and fees
Sterling Breeze by Panhandle Getaways

Perfect Little Paradise !! VERY COZY UNIT WITH SPECTACULAR VIEW!!!

Perfect Little Paradise !! VERY COZY UNIT WITH SPECTACULAR VIEW!!!
Panama City Beach
9.6 out of 10, Exceptional, (101 reviews)
"This little place was perfect for our little family! Very clean and cozy. Overall just a wonderful experience. "
United States
Alexis T.
$406 nightly
The price is $453
Jul 8 - Jul 9
Total with taxes and fees
Perfect Little Paradise !! VERY COZY UNIT WITH SPECTACULAR VIEW!!!

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, (254 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
$350 nightly
The price is $390
Jul 12 - Jul 13
Total with taxes and fees
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!
Panama City Beach
9.8 out of 10, Exceptional, (136 reviews)
"Very nice smaller condo right near the beach, convenient to everything."
United States
David H.
$440 nightly
The price is $491
Jul 8 - Jul 9
Total with taxes and fees
Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

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, (29 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
$612 nightly
The price is $692
Jul 7 - Jul 8
Total with taxes and fees
Calypso Tower 3 by Panhandle Getaways

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.4 out of 10, Exceptional, (124 reviews)
"Room had an excellent view. Very clean, we will definitely be back!"
United States
Shirley B.
$294 nightly
The price is $309
Jul 25 - Jul 26
Total with taxes and fees
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
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 $282 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?

Margaritaville Resort | 6BR Beach Oasis | Pool: Visitors like this Chipley vacation home rental. It is located on the beach and offers a private balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen 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 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. In the larger area, you’ll find Pal's Park and Moss Hill Methodist Church.

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.