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

Chipley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chipley vacation rentals

A laundry room with a washing machine and a sign above the door that reads "Lost Socks Seeking Sole Mates".

1. Sparrow

Sparrow
3.0 star property
Lynn Haven
8.6 out of 10, Excellent, (4 reviews)
"Great neighborhood. I didn’t know what to expect with it being a converted garage area but it was great! Had everything we needed for our weekend stay."
United States
Cateria
$135 nightly
The price is $140
Oct 18 - Oct 19
Total with taxes and fees
Sparrow
A modern living room with a sofa, coffee table, and dining area.

2. Georgia

Georgia
3.0 star property
Lynn Haven
2.0 out of 10, (1 review)
"The place looked a little better in the photos. Only stayed an hour because there were mosquitoes everywhere in our room and we were getting eaten alive. Waist of money."
United States
Dajae
$166 nightly
The price is $173
Sep 27 - Sep 28
Total with taxes and fees
Georgia
A kitchen with wooden cabinets, stainless steel appliances, a central island with bar stools, and a decorative wreath on the wall.

3. Michigan

Michigan
3.5 star property
Lynn Haven
4.0 out of 10, (1 review)
"The listing was misleading. I did not realize I was renting the pool house in the backyard. A family and I both pulled up in the driveway at the same time. They had the house that I thought I was renting and I was in the pool house. It was definitely awkward. The property definitely needs some maintenance and updating. The entire unit smelled like a weed festival."
United States
cynthia
$159 nightly
The price is $166
Oct 18 - Oct 19
Total with taxes and fees
Michigan
A beach with rows of sun loungers and umbrellas, a clear blue sky, and the ocean in the background.

4. 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, (201 reviews)
"Immaculate view"
United States
Marcus
$457 nightly
The price is $517
Sep 23 - Sep 24
Total with taxes and fees
Tidewater Beach Resort by Panhandle Getaways
A beach with rows of blue umbrellas and white beach chairs, a sandy shore, and the ocean in the background.

5. Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (39 reviews)
"The property was very clean and in an excellent location . We weren’t on the beach , but we had a great view of the ocean and the pools I would highly recommend"
United States
Thomas
$520 nightly
The price is $588
Sep 27 - Sep 28
Total with taxes and fees
Calypso Tower 3 by Panhandle Getaways
A beach with clear blue water, a pier, and rows of blue beach umbrellas.

6. 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 24 - Sep 25
Total with taxes and fees
Calypso Beach Resort Tower 1
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and white chairs.

7. 3BR Canal-front Home w/ Wifi & Boat Dock

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
$450 nightly
The price is $482
Sep 30 - Oct 1
Total with taxes and fees
3BR Canal-front Home w/ Wifi & Boat Dock
A balcony with a view of the beach and ocean, featuring a table and chairs.

8. 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, (9 reviews)
"My stay was excellent however I think we needed linen replacements for the duration of the stay"
United States
andre
$773 nightly
The price is $860
Oct 9 - Oct 10
Total with taxes and fees
Calypso Resort and Towers by Book That Condo
A wide sandy beach with footprints, a clear blue sky, and a distant pier.

9. 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 25 - Sep 26
Total with taxes and fees
Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court
A wooden deck with a table and chairs overlooking a beach.

10. Beach House - Sky’s the Limit

Beach House - Sky’s the Limit
3.5 star property
Panama City Beach
$876 nightly
The price is $991
Oct 9 - Oct 10
Total with taxes and fees
Beach House - Sky’s the Limit
A resort with a pool area, beach, and ocean view.

11. Grand Panama Beach Resort - PET Friendly by Panhandle Getaways

Grand Panama Beach Resort - PET Friendly by Panhandle Getaways
3.5 star property
Panama City Beach
6.6 out of 10, (8 reviews)
"Great location nice room "
United States
Joshua
$480 nightly
The price is $543
Sep 24 - Sep 25
Total with taxes and fees
Grand Panama Beach Resort - PET Friendly by Panhandle Getaways
A beach view with a pier extending into the ocean, clear skies, and a balcony overlooking the scene.

12. Calypso Beach Resort Tower 2 by Panhandle Getaways

Calypso Beach Resort Tower 2 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (193 reviews)
"Gorgeous view of the ocean. The condo was really nice and modern. This was our first time staying at the Calypso. We will definitely be back!"
United States
Cheryl
$553 nightly
The price is $626
Sep 23 - Sep 24
Total with taxes and fees
Calypso Beach Resort Tower 2 by Panhandle Getaways
A beach with clear turquoise water and a sandy shore.

13. Studios at Fontainebleau Terrace

Studios at Fontainebleau Terrace
3.5 star property
Panama City Beach
7.0 out of 10, Good, (4 reviews)
"Nice employees clean room would have been perfect if it had a private balcony will come visit again! "
United States
Nicholas
$229 nightly
The price is $259
Sep 24 - Sep 25
Total with taxes and fees
Studios at Fontainebleau Terrace
A balcony with blue chairs overlooking a beach and a pier.

14. Tidewater

Tidewater
3.5 star property
Panama City Beach
6.0 out of 10, (3 reviews)
"Road construction directly in front of condo was bad. The staff and the people at the desk were very friendly and helpful. The property was kept clean. "
United States
Robert
$422 nightly
The price is $477
Sep 29 - Sep 30
Total with taxes and fees
Tidewater
A coastal hotel with a pool, beachfront access, and a view of the ocean.

15. Coastal Condo 807 by Brightwild Beachfront

Coastal Condo 807 by Brightwild Beachfront
2.0 star property
Panama City Beach
$493 nightly
The price is $558
Sep 29 - Sep 30
Total with taxes and fees
Coastal Condo 807 by Brightwild Beachfront
A balcony with a glass table and chairs, overlooking a beach and the ocean.

16. Aquavista 804e

Aquavista 804e
2.5 star property
Panama City Beach
$365 nightly
The price is $383
Sep 30 - Oct 1
Total with taxes and fees
Aquavista 804e
A bedroom with a large bed, ceiling fans, a TV, and a view of the ocean.

17. Beach House - Sunset Paradise by PHG

Beach House - Sunset Paradise by PHG
3.5 star property
Bahama Beach
$474 nightly
The price is $536
Sep 23 - Sep 24
Total with taxes and fees
Beach House - Sunset Paradise by PHG
A covered porch with a hammock, a potted plant, and a view of neighboring houses.

18. Cottage on Cabana Private Gated Neighborhood

Cottage on Cabana Private Gated Neighborhood
3.0 star property
Panama City Beach
$534 nightly
The price is $598
Oct 4 - Oct 5
Total with taxes and fees
Cottage on Cabana Private Gated Neighborhood
A modern kitchen with a stainless steel refrigerator, a built-in oven, and a large island with seating.

19. Sandbar Serenade by Avantstay Beachside Home + Pool + Tennis Court + Beach Access + Near Pier Park

Sandbar Serenade by Avantstay Beachside Home + Pool + Tennis Court + Beach Access + Near Pier Park
3.0 star property
Panama City Beach
6.0 out of 10, (1 review)
$331 nightly
The price is $375
Sep 23 - Sep 24
Total with taxes and fees
Sandbar Serenade by Avantstay Beachside Home + Pool + Tennis Court + Beach Access + Near Pier Park
A modern living room with a grey sofa, a white coffee table, a mounted TV, and a potted plant.

20. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
$391 nightly
The price is $442
Sep 23 - Sep 24
Total with taxes and fees
Octa Collection on Front Beach
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

The Flamingo Hotel and Tower

The Flamingo Hotel and Tower

8/10 Good
"I always enjoy my stay at the Flamingo!!"
Kimberly 1-night trip
Posted 1 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 $87 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 7 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.