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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chipley vacation rentals

A bed with a textured grey mattress, a headboard with vertical lines, and three pillows with text and patterns.

1. The Cozy Farmhouse Retreat

The Cozy Farmhouse Retreat
Chipley
$418 nightly
The price is $456
Oct 26 - Oct 27
Total with taxes and fees
The Cozy Farmhouse Retreat
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.
$139 nightly
The price is $151
Oct 19 - Oct 20
Total with taxes and fees
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
An indoor swimming pool with a view of the outside.

3. 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.
$219 nightly
The price is $239
Oct 18 - Oct 19
Total with taxes and fees
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Property grounds

4. 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.
$165 nightly
The price is $180
Nov 2 - Nov 3
Total with taxes and fees
Cozy Lakefront Airstream
A wooden staircase leading to a house with a deck, surrounded by trees and a lawn.

5. 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.
$269 nightly
The price is $287
Oct 18 - Oct 19
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.

6. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (56 reviews)
"The house was amazing. We really enjoyed our stay and it was in a great location. Would definitely stay again."
United States
Jordan B.
$330 nightly
The price is $368
Oct 28 - Oct 29
Total with taxes and fees
~ La Conchita ~ w private pool & Firepit
A beach view with a pier extending into the ocean, clear skies, and a balcony overlooking the scene.

7. 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, (196 reviews)
"The room and view were absolutely amazing!"
United States
Brittany
$553 nightly
The price is $626
Oct 18 - Oct 19
Total with taxes and fees
Calypso Beach Resort Tower 2 by Panhandle Getaways
A wooden boardwalk leading to a beach with a pier extending into the ocean.

8. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Panama City
10.0 out of 10, Exceptional, (23 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
$263 nightly
The price is $294
Oct 19 - Oct 20
Total with taxes and fees
Private - Waterfront Cottage - Panama City, FL
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
9.0 out of 10, Wonderful, (31 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
$332 nightly
The price is $361
Oct 18 - Oct 19
Total with taxes and fees
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
A beach with clear blue water, a pier, and rows of blue beach umbrellas.

10. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (14 reviews)
"My wife and I loved that everything was close by. Qill definitely stay again 10/10"
United States
shawn
$486 nightly
The price is $550
Oct 19 - Oct 20
Total with taxes and fees
Calypso Beach Resort Tower 1
A beach with rows of blue umbrellas and white beach chairs, a sandy shore, and the ocean in the background.

11. 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, (41 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
$486 nightly
The price is $550
Oct 18 - Oct 19
Total with taxes and fees
Calypso Tower 3 by Panhandle Getaways
A bedroom with a bed, a framed sign on the wall, and a door.

12. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
$311 nightly
The price is $352
Oct 18 - Oct 19
Total with taxes and fees
Octa Collection on Front Beach
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13. 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.
$241 nightly
The price is $269
Nov 3 - Nov 4
Total with taxes and fees
Origin 0538- Studio - Breath Taking Gulf Views
A beach with a long pier extending into the ocean, white sand, and clear blue water.

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

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.6 out of 10, Exceptional, (137 reviews)
"Great little place to stay and the views were nice!"
United States
Andres
$175 nightly
The price is $184
Nov 10 - Nov 11
Total with taxes and fees
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
A balcony with a view of a beach, a palm tree, and a 'No Smoking' sign.

15. Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.4 out of 10, Exceptional, (24 reviews)
"The room was clean and had everything we needed for our stay. The view from the front door of the beach was beautiful! I would stay with them again!"
United States
Whitney F.
$348 nightly
The price is $388
Nov 2 - Nov 3
Total with taxes and fees
Newly renovated studio on the beach # 304
A pool area with a fountain, lounge chairs, and a view of the ocean.

16. 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
Oct 18 - Oct 19
Total with taxes and fees
Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!
A room with a view of the beach, a wooden table, and white chairs.

17. Emerald Beach Resort by Panhandle Getaways

Emerald Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.6 out of 10, Excellent, (29 reviews)
"Everything was perfect. Really good experience "
United States
Senad
$518 nightly
The price is $586
Oct 18 - Oct 19
Total with taxes and fees
Emerald Beach Resort by Panhandle Getaways
A balcony with blue chairs overlooking a beach and a pier.

18. 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
$308 nightly
The price is $343
Oct 25 - Oct 26
Total with taxes and fees
Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!
A beach view from a balcony with a pool and lounge chairs.

19. Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!

Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!
Panama City Beach
9.2 out of 10, Wonderful, (187 reviews)
"This was an amazing stay for my daughter’s spring break. We did have an issue with the door not locking, and the team was quick to come resolve the issue. Would def stay here again!"
United States
Amber B.
$526 nightly
The price is $587
Oct 18 - Oct 19
Total with taxes and fees
Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!
A beach with clear turquoise waters and a sandy shoreline.

20. Ocean view from the 13th Floor. Owner Operated.

Ocean view from the 13th Floor. Owner Operated.
Panama City Beach
9.8 out of 10, Exceptional, (277 reviews)
"Had an incredible time. It was the perfect place to stay with my family."
United States
Kelli
$286 nightly
The price is $319
Nov 2 - Nov 3
Total with taxes and fees
Ocean view from the 13th Floor. Owner Operated.
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

Beachcomber Beachfront Hotel, a By The Sea Resort

Beachcomber Beachfront Hotel, a By The Sea Resort

8/10 Good
"We enjoyed our stay. The staff was lovely. The bathrooms could use updating, but we had everything we needed. It was right after the hurricane, so pool was as messed up, but they got it going before we left. Best feature- the beach… just gorgeous."
Martin 4-night trip
Posted 3 hours ago
Beachcomber Beachfront Hotel, a By The Sea Resort

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 $191 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.