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Chipley Vacation Rentals

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Our top choices for Chipley vacation rentals

Mobile Home in Chipley

Cozy Lakefront Airstream
9.8 out of 10, Exceptional, (14)
"We loved the property, enjoyed all the amenities and relaxed comfortably."
United States
Lesley H.
$153 nightly
The price is $166
Jan 6 - Jan 7, 2026
Total with taxes and fees
Cozy Lakefront Airstream
10.0 out of 10, Exceptional, (3)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
$177 nightly
The price is $193
Jan 5 - Jan 6, 2026
Total with taxes and fees
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
9.6 out of 10, Exceptional, (23)
"Great stay! Very peaceful river setting! Great host! "
United States
Mike A.
$243 nightly
The price is $259
Jan 6 - Jan 7, 2026
Total with taxes and fees
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
10.0 out of 10, Exceptional, (27)
"According to our friends the stay was very peaceful and very relaxing for them."
United States
Ken N.
$116 nightly
The price is $123
Jan 7 - Jan 8, 2026
Total with taxes and fees
Private Cozy bedroom with on suite living room

Aparthotel in Panama City Beach

Origin At Seahaven
3.5 star property
7.0 out of 10, Good, (2171)
"Room was great loved the contactless "
United States
Avontay
$193 nightly
The price is $219
Jan 6 - Jan 7, 2026
Total with taxes and fees
Origin At Seahaven
9.6 out of 10, Exceptional, (11)
"Enough room for 2 and wonderful bed"
United States
Angel C.
$130 nightly
The price is $143
Jan 3 - Jan 4, 2026
Total with taxes and fees
Beach Guest House Cottage Pier Park, Frank Brown Park, & 30a, private driveway
9.0 out of 10, Wonderful, (64)
"I loved being able to walk out the door down the deck and straight to dock to boat. It was very clean on the inside, I will stay here again"
United States
Allen G.
$305 nightly
The price is $324
Jan 4 - Jan 5, 2026
Total with taxes and fees
Dog-Friendly Retreat with Private Dock & Water Views - Great for Fishing & Boating

Vacation Home in Panama City

~ La Conchita 🐚 ~ w private pool!
9.8 out of 10, Exceptional, (49)
"Very clean and comfortable. Would definitely recommend for a family."
United States
Neil L.
$288 nightly
The price is $321
Jan 3 - Jan 4, 2026
Total with taxes and fees
~ La Conchita 🐚 ~ w private pool!

Condo in Panama City Beach

Grand Panama Beach Resort
4.0 star property
6.4 out of 10, (5)
"Nice!"
United States
Erik
$367 nightly
The price is $415
Jan 4 - Jan 5, 2026
Total with taxes and fees
Grand Panama Beach Resort
9.6 out of 10, Exceptional, (62)
"Great place to stay. Parking for 2 vehicles . Three vehicles kinda sketchy. Overall excellent stay"
United States
John F.
$370 nightly
The price is $409
Jan 25 - Jan 26, 2026
Total with taxes and fees
Private Pool Private Yard "Golf Cart Rentals Available locally"

Aparthotel in Panama City Beach

Landmark Holiday Beach
3.5 star property
8.6 out of 10, Excellent, (222)
"Kitchen has everything you need along with washer and dryer.. Beautiful beachfront view ."
United States
Judy
Landmark Holiday Beach

Vacation Home in Panama City

The Banana, A Peaceful Getaway
9.6 out of 10, Exceptional, (24)
"Excellent stay! Will be back!"
United States
Nathan T.
$203 nightly
The price is $216
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Banana, A Peaceful Getaway
9.4 out of 10, Exceptional, (108)
"Covered parking, nice location, clean comfortable room, close to the Pier. Great Sunset views!..... "
United States
Gerald L.
$165 nightly
The price is $173
Jan 7 - Jan 8, 2026
Total with taxes and fees
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
9.2 out of 10, Wonderful, (32)
"In the middle of everything. Easy to get around and to get to beach. "
United States
Suzy V.
$219 nightly
The price is $244
Jan 4 - Jan 5, 2026
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views

Apartment in Panama City Beach

Newly renovated studio on the beach # 304
2.0 star property
9.4 out of 10, Exceptional, (9)
"Everything was as promised and the communication with the property manager was perfect as well!!"
United States
Christy T.
$200 nightly
The price is $224
Jan 10 - Jan 11, 2026
Total with taxes and fees
Newly renovated studio on the beach # 304
9.2 out of 10, Wonderful, (68)
"Amazing find. Very clean updated room . Comfortable bed . On the beach ,close walk to water . Near Sharkey's restaurant. I would love to stay here again on my next visit. "
United States
Kimberly C.
$257 nightly
The price is $284
Jan 4 - Jan 5, 2026
Total with taxes and fees
Oceanfront studio with shared pool & washer/dryer - steps from the beach
9.2 out of 10, Wonderful, (123)
"Beautiful view somewhat dated interior. Only stayed one night as we had a week planned in Seacrest and needed one additional night. Parking was full when we arrived very late ( peak season). "
United States
George Z.
$388 nightly
The price is $432
Jan 5 - Jan 6, 2026
Total with taxes and fees
BEACHFRONT CONDO NOW ACCEPTING RENTALS!!
9.4 out of 10, Exceptional, (79)
"Condo was very comfortable and beautiful view of the ocean. "
United States
Anonymous traveler
$473 nightly
The price is $525
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sea Breeze-PCB-Deluxe Beachfront King Main Suite-2 baths-Sea Breezes Await!
9.2 out of 10, Wonderful, (52)
"Pool,condo , beach& the Whole property was wonderful & had everything we wanted & needed."
United States
Linda T.
$520 nightly
The price is $575
Jan 3 - Jan 4, 2026
Total with taxes and fees
Oceanfront Paradise! with Beach Chairs, and Free Activities Each Day +More
9.0 out of 10, Wonderful, (126)
"This was an awesome place stay. We will keep on our favorites list. "
United States
Kenneth W.
$433 nightly
The price is $473
Jan 22 - Jan 23, 2026
Total with taxes and fees
Free Beach Chair Service + Free Activities! Summer Deals! 17th Floor!
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 $173 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?

"Tide Life" - Perfect Sized Family Beach House: You might want to consider this vacation home rental near Chipley, which is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 8 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.