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

Chipley Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chipley vacation rentals

An indoor swimming pool with a view of the outside.

1. Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Carrie P.
$222 nightly
The price is $242
Sep 30 - Oct 1
Total with taxes and fees
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
An indoor swimming pool with a long, narrow shape, surrounded by walls with large windows.

2. 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.
$141 nightly
The price is $153
Oct 20 - Oct 21
Total with taxes and fees
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Property grounds

3. 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.
$180 nightly
The price is $197
Oct 24 - Oct 25
Total with taxes and fees
Cozy Lakefront Airstream
A wooden staircase leading to a house with a deck, surrounded by trees and a lawn.

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, (36 reviews)
"Amazing place"
United States
Alex R.
$235 nightly
The price is $251
Oct 1 - Oct 2
Total with taxes and fees
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
A beach with clear turquoise water, a sandy shore, and buildings in the background.

5. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (56 reviews)
"Great location!Kids loved the pool even if it was cold. The owners were amazing, and quick to respond."
United States
Ellen D.
$310 nightly
The price is $348
Oct 16 - Oct 17
Total with taxes and fees
~ La Conchita ~ w private pool & Firepit
A wide sandy beach with footprints, a clear blue sky, and a distant pier.

6. Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court

Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court
4.0 star property
Panama City Beach
10.0 out of 10, Exceptional, (1 review)
"Great area !!"
United States
Diana
$366 nightly
The price is $414
Sep 30 - Oct 1
Total with taxes and fees
Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court
A wooden boardwalk leading to a beach with a pier extending into the ocean.

7. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (21 reviews)
"Very clean and unique hidden gem of panama city, it may be in the city but you cant tell while at the house. Its extremely private and secluded, wildlife was everywhere, we watch herons and ducks in the bayou behind the house, a fox and a family of possums in the back yard after dusk. Its dog friendly and close to a lot of dog friendly restaurants, it also has a kayak launch and the fishing is incredible in the bayou. We caught multiple trout and reddish. Ill be posting a video on youtube @...
United States
William
$273 nightly
The price is $305
Oct 5 - Oct 6
Total with taxes and fees
Private - Waterfront Cottage - Panama City, FL
A beach with clear blue water, a pier, and rows of blue beach umbrellas.

8. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (13 reviews)
"My wife and I loved that everything was close by. Qill definitely stay again 10/10"
United States
shawn
$503 nightly
The price is $569
Sep 30 - Oct 1
Total with taxes and fees
Calypso Beach Resort Tower 1
A beach with clear turquoise water, a sandy shore, and a few buildings in the distance.

9. 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, (30 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
$334 nightly
The price is $363
Oct 1 - Oct 2
Total with taxes and fees
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
A balcony with two white Adirondack chairs and a small round table with a vase of yellow flowers and two black mugs.

10. Celadon 15th private parking + Beach Chair Service!

Celadon 15th private parking + Beach Chair Service!
Panama City Beach
10.0 out of 10, Exceptional, (180 reviews)
"We absolutely had the best vacation at PCB. "
United States
Tracy D.
$351 nightly
The price is $391
Oct 7 - Oct 8
Total with taxes and fees
Celadon 15th private parking + Beach Chair Service!
326681007_1221068595167246_3835672466794079402_n

11. 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.
$246 nightly
The price is $274
Sep 30 - Oct 1
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views
A balcony with a view of the ocean, a grill, and a seating area.

12. Sterling Breeze by Panhandle Getaways

Sterling Breeze by Panhandle Getaways
3.5 star property
Panama City Beach
8.6 out of 10, Excellent, (40 reviews)
"Room was nice"
United States
Christopher
$495 nightly
The price is $560
Sep 30 - Oct 1
Total with taxes and fees
Sterling Breeze by Panhandle Getaways
A sandy beach path leading to the ocean, surrounded by dunes and a wooden fence.

13. Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!

Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!
Panama City Beach
9.2 out of 10, Wonderful, (29 reviews)
"Everything was great!! The location was awesome!! We had a great time!!!"
United States
Jason W.
$397 nightly
The price is $444
Oct 10 - Oct 11
Total with taxes and fees
Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!
A balcony with a view of a beach and ocean.

14. Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza

Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza
Panama City Beach
9.4 out of 10, Exceptional, (159 reviews)
"We absolutely loved staying here. The condo was very nice and all the amenities on the property were amazing. The host was very responsive."
United States
Kelsey C.
$446 nightly
The price is $497
Sep 30 - Oct 1
Total with taxes and fees
Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza
A balcony with a view of the ocean, a table with chairs, and a vase with flowers.

15. Beautiful Condo with beach view free beach service, wifi and 10% weekly discount

Beautiful Condo with beach view free beach service, wifi and 10% weekly discount
Panama City Beach
9.4 out of 10, Exceptional, (142 reviews)
"The kitschy had everything we could possibly need and more. The rooms were spacious and laid out perfectly for our needs. Beautiful view from balcony "
United States
Jim L.
Beautiful Condo with beach view free beach service, wifi and 10% weekly discount
A balcony with blue chairs overlooking a beach and a pier.

16. Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!

Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!
Panama City Beach
9.6 out of 10, Exceptional, (12 reviews)
"Excellent location to and the complimentary two beach chairs and beach umbrella was amazing."
United States
Paulo
$327 nightly
The price is $364
Oct 2 - Oct 3
Total with taxes and fees
Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!
A pool area with a fountain, lounge chairs, and a view of the ocean.

17. 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, (139 reviews)
"Great stay."
United States
John S.
$404 nightly
The price is $451
Sep 30 - Oct 1
Total with taxes and fees
Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!
A hotel pool area with a sunset view, a pool, and outdoor seating.

18. 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
9.2 out of 10, Wonderful, (190 reviews)
"We love staying at Grand Panama. Been there several times and it’s always wonderful."
United States
Nicole R.
$503 nightly
The price is $562
Oct 7 - Oct 8
Total with taxes and fees
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!
A modern living room with a sofa, a coffee table, and a large sliding glass door leading to a balcony with a view of the ocean.

19. Polynesian #104 Ground Level

Polynesian #104 Ground Level
Panama City Beach
8.4 out of 10, Very good, (65 reviews)
"Great location and view! "
United States
kerri m.
$209 nightly
The price is $233
Oct 24 - Oct 25
Total with taxes and fees
Polynesian #104 Ground Level
A resort with multiple swimming pools, beach areas, and palm trees.

20. [5 O'Clock Somewhere] Gorgeous Edgewater Beach Resort Panama City Beach, Florida

[5 O'Clock Somewhere] Gorgeous Edgewater Beach Resort Panama City Beach, Florida
Panama City Beach
9.6 out of 10, Exceptional, (146 reviews)
"Great location. Short walk to the beach, and beautiful pool area."
United States
Caralyn H.
$262 nightly
The price is $292
Oct 1 - Oct 2
Total with taxes and fees
[5 O'Clock Somewhere] Gorgeous Edgewater Beach Resort Panama City Beach, Florida
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chipley Hotel Reviews

The Flamingo Hotel and Tower

The Flamingo Hotel and Tower

10/10 Excellent
"This is by far the BEST budget hotel in PCB, staff are always 10-10, and its always a fun place to stay!!"
Lee 1-night trip
Posted less than an hour ago
The Flamingo Hotel and Tower

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 $202 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?

Beach House - Sunset Paradise by PHG: You might want to consider this Chipley vacation home rental for your stay. It 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 Pal's Park are a couple of lovely local spots to get outside and enjoy nature. Lucas Lake 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.