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
Jun 9 - Jun 10
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, (4 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
$215 nightly
The price is $235
Jun 2 - Jun 3
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
$168 nightly
The price is $184
Jun 2 - Jun 3
Total with taxes and fees
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

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, (27 reviews)
"Amazing place"
United States
Alex R.
$245 nightly
The price is $261
Jun 2 - Jun 3
Total with taxes and fees
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

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
Jun 8 - Jun 9
Total with taxes and fees
Pelican's Nest - The Hideaway in Panama City

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, (182 reviews)
"Nice view. Good communication with escala host"
United States
Lori V.
$533 nightly
The price is $595
Jun 7 - Jun 8
Total with taxes and fees
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

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

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
$461 nightly
The price is $491
Jun 7 - Jun 8
Total with taxes and fees
3BR Canal-front Home w/ Wifi & Boat Dock

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.
$267 nightly
The price is $298
Jun 2 - Jun 3
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views

Splash Beach Resort by Panhandle Getaways

Splash Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
7.4 out of 10, Good, (211 reviews)
"View was excellent. "
United States
Ronald
$481 nightly
The price is $540
Jun 2 - Jun 3
Total with taxes and fees
Splash 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, (252 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
$330 nightly
The price is $367
Jun 7 - Jun 8
Total with taxes and fees
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Ocean-front Master Bedroom with Spectacular View!!!

Ocean-front Master Bedroom with Spectacular View!!!
Panama City Beach
9.4 out of 10, Exceptional, (146 reviews)
"Excellent stay, great view. "
United States
Richard T.
$379 nightly
The price is $423
Jun 11 - Jun 12
Total with taxes and fees
Ocean-front Master Bedroom with Spectacular View!!!

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,186 reviews)
"It was a nice stay. Room was really nice. "
United States
Paul
$234 nightly
The price is $265
Jun 3 - Jun 4
Total with taxes and fees
Origin At Seahaven

Fountain of Youth Edgewater Villa 955-Tranquil Pond Views! Free Beach Tram! Remodeled Condo!

Fountain of Youth Edgewater Villa 955-Tranquil Pond Views! Free Beach Tram! Remodeled Condo!
Panama City Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great place"
United States
Benjamin C.
$547 nightly
The price is $609
Jun 27 - Jun 28
Total with taxes and fees
Fountain of Youth Edgewater Villa 955-Tranquil Pond Views! Free Beach Tram! Remodeled Condo!

Beach getaway just 100 yards from the beach.

Beach getaway just 100 yards from the beach.
Laguna Beach
10.0 out of 10, Exceptional, (100 reviews)
"Would stay again, nice place"
United States
Leigh
$347 nightly
The price is $384
Jun 6 - Jun 7
Total with taxes and fees
Beach getaway just 100 yards from the beach.

Lovely Townhouse Steps From Beach w/Free WiFi, Breathtaking Views, & Central AC

Lovely Townhouse Steps From Beach w/Free WiFi, Breathtaking Views, & Central AC
Sunnyside
9.6 out of 10, Exceptional, (26 reviews)
"Perfect location for a family vacation! "
United States
Lorrie G.
$440 nightly
The price is $487
Jun 10 - Jun 11
Total with taxes and fees
Lovely Townhouse Steps From Beach w/Free WiFi, Breathtaking Views, & Central AC

Dog-Friendly Poolside Retreat Near the Beach with Room for the Family

Dog-Friendly Poolside Retreat Near the Beach with Room for the Family
Panama City Beach
9.4 out of 10, Exceptional, (33 reviews)
"The location was great. The access to the pool was awesome. Everything was in walking distance. The couch and chairs needs to be replaced and it had dog hair everywhere. "
United States
Bianca S.
$677 nightly
The price is $737
Jun 21 - Jun 22
Total with taxes and fees
Dog-Friendly Poolside Retreat Near the Beach with Room for the Family

Beautiful PCB Townhome: Balcony & Resort Amenities

Beautiful PCB Townhome: Balcony & Resort Amenities
4.0 star property
Panama City Beach
10.0 out of 10, Exceptional, (2 reviews)
"Yes, everything was good and I like how the places to shop and eat were also close by."
United States
Ketline
$380 nightly
The price is $426
Jun 3 - Jun 4
Total with taxes and fees
Beautiful PCB Townhome: Balcony & Resort Amenities

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, (133 reviews)
"Very nice smaller condo right near the beach, convenient to everything."
United States
David H.
$439 nightly
The price is $490
Jun 2 - Jun 3
Total with taxes and fees
Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

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, (106 reviews)
"Our room had a beach front view. The room was very clean and spacious. The bed slept great! We would definitely stay again. "
United States
Leslie
$723 nightly
The price is $818
Jun 6 - Jun 7
Total with taxes and fees
Grand Panama Beach Resort by Panhandle Getaways

Beachfront!! Free Beach Chairs!! Over 297 Five Star Reviews!

Beachfront!! Free Beach Chairs!! Over 297 Five Star Reviews!
Miramar Beach
10.0 out of 10, Exceptional, (298 reviews)
"Very nice condo right on Panama City Beach. Property was clean and nice and having two pool options was a real plus. The beach was beautiful and not too crowded at any point of the trip. I would recommend this rental for sure."
United States
Tom
$455 nightly
The price is $508
Jun 18 - Jun 19
Total with taxes and fees
Beachfront!! Free Beach Chairs!! Over 297 Five Star Reviews!
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 $525 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.

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?

❃ Walkable to Food & Fun ❃ Beach-Front Pool ❃ Canal-Side Home ❃ No Pet Fee: You might want to consider this vacation home rental near Chipley, which is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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. 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.