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

Chipley Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chipley holiday rentals

Pool

1. 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.
The price is HK$664
HK$1,194 total
includes taxes & fees
21 Sept - 22 Sept
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Indoor pool, a heated pool

2. 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.
The price is HK$953
HK$1,874 total
includes taxes & fees
18 Sept - 19 Sept
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
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.
The price is HK$883
HK$1,306 total
includes taxes & fees
22 Sept - 23 Sept
Cozy Lakefront Airstream
Property grounds

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, (35 reviews)
"Amazing place"
United States
Alex R.
The price is HK$1,177
HK$2,056 total
includes taxes & fees
18 Sept - 19 Sept
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Beach nearby, sun-loungers

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.
The price is HK$1,059
HK$3,224 total
includes taxes & fees
22 Sept - 23 Sept
~ La Conchita ~ w private pool & Firepit
On the beach

6. Gulf Front Escape with Private Balcony and Pool

Gulf Front Escape with Private Balcony and Pool
Laguna Beach
9.8 out of 10, Exceptional, (31 reviews)
"Great stay! Peaceful and quiet location, but close to everything."
United States
Rachel M.
The price is HK$790
HK$3,040 total
includes taxes & fees
27 Sept - 28 Sept
Gulf Front Escape with Private Balcony and Pool
Beach nearby

7. 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, (28 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is HK$698
HK$2,758 total
includes taxes & fees
22 Sept - 23 Sept
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
View from room

8. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (11 reviews)
"My wife and I loved that everything was close by. Qill definitely stay again 10/10"
United States
shawn
The price is HK$1,083
HK$4,961 total
includes taxes & fees
22 Sept - 23 Sept
Calypso Beach Resort Tower 1
Property grounds

9. 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, (11 reviews)
"Excellent location to and the complimentary two beach chairs and beach umbrella was amazing."
United States
Paulo
The price is HK$687
HK$2,806 total
includes taxes & fees
21 Sept - 22 Sept
Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!
Property grounds

10. Perfect Little Paradise ☀️👙🐬!! STILL AVAILABLE FOR LABOR DAY

Perfect Little Paradise ☀️👙🐬!! STILL AVAILABLE FOR LABOR DAY
Panama City Beach
9.6 out of 10, Exceptional, (107 reviews)
"The establishment was clean, the view was nice and the host was very personable"
United States
Jeffery S.
Perfect Little Paradise ☀️👙🐬!! STILL AVAILABLE FOR LABOR DAY
Outdoor pool, a heated pool

11. 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.
The price is HK$628
HK$4,230 total
includes taxes & fees
19 Sept - 20 Sept
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!
Beach nearby

12. 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.
The price is HK$620
HK$2,212 total
includes taxes & fees
1 Oct - 2 Oct
Origin 0538- Studio - Breath Taking Gulf Views
Smart TV, books

13. OCEANFRONT! RIGHT ON THE BEACH!! Free Beach Chairs! 188 5 Star Reviews!

OCEANFRONT! RIGHT ON THE BEACH!! Free Beach Chairs! 188 5 Star Reviews!
Miramar Beach
10.0 out of 10, Exceptional, (201 reviews)
"Enjoyable stay."
United States
Angela P.
The price is HK$1,145
HK$3,685 total
includes taxes & fees
24 Sept - 25 Sept
OCEANFRONT! RIGHT ON THE BEACH!! Free Beach Chairs! 188 5 Star Reviews!
On the beach, sun-loungers

14. Beachfront Luxe @ Splash 1203E • Fireplace • Recliners

Beachfront Luxe @ Splash 1203E • Fireplace • Recliners
Panama City Beach
9.8 out of 10, Exceptional, (89 reviews)
"The perfect little place for my family and I to relax, unwind and enjoy the beach."
United States
Lisa R.
The price is HK$1,262
HK$3,754 total
includes taxes & fees
27 Sept - 28 Sept
Beachfront Luxe @ Splash 1203E • Fireplace • Recliners
Outdoor pool, a heated pool

15. Private Heated Pool Tiki Bar Oasis Walk to Beach

Private Heated Pool Tiki Bar Oasis Walk to Beach
Sunnyside
10.0 out of 10, Exceptional, (13 reviews)
"Phenomenal experience and great stay. Would recommend to anyone wanting a true getaway!"
United States
Alex D.
The price is HK$1,906
HK$5,036 total
includes taxes & fees
23 Sept - 24 Sept
Private Heated Pool Tiki Bar Oasis Walk to Beach
Property grounds

16. Ocean-front Master Bedroom with Spectacular View!!!

Ocean-front Master Bedroom with Spectacular View!!!
Panama City Beach
9.4 out of 10, Exceptional, (155 reviews)
"My family had a great time here."
United States
Christopher B.
The price is HK$940
HK$2,649 total
includes taxes & fees
24 Sept - 25 Sept
Ocean-front Master Bedroom with Spectacular View!!!
View from room

17. 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, (120 reviews)
"Great view and helpful staff."
United States
Terri
The price is HK$1,499
HK$5,920 total
includes taxes & fees
22 Sept - 23 Sept
Grand Panama Beach Resort by Panhandle Getaways
On the beach, white sand

18. 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, (38 reviews)
"Loved the view of the ocean. Condo was nice an clean. Everything was great! Will be back."
United States
Jamie
The price is HK$966
HK$4,687 total
includes taxes & fees
15 Oct - 16 Oct
Calypso Tower 3 by Panhandle Getaways
On the beach

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

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.4 out of 10, Exceptional, (136 reviews)
"Great little place to stay and the views were nice!"
United States
Andres
The price is HK$628
HK$1,496 total
includes taxes & fees
23 Sept - 24 Sept
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Property grounds

20. Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park

Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park
Panama City Beach
9.6 out of 10, Exceptional, (27 reviews)
"The room was very clean and well taken care of! Would stay there again!"
United States
Kiley S.
The price is HK$1,059
HK$3,296 total
includes taxes & fees
20 Sept - 21 Sept
Tidewater - Breathtaking first-line ocean views! Walking distance to Pier Park
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
"The view was amazing. The pool, hot tub, and poolside bar were nice just closed too early. The elevators were very sketchy but other than that had a great stay!"
Melissa 6-night trip
Posted 9 hours ago
Beachcomber Beachfront Hotel, a By The Sea Resort

Find out more about Chipley

Search for holiday rentals in Chipley on Expedia! You can easily find your home rentals, villas, holiday apartments in Chipley using one of the methods below:

  • View our selection of featured holiday rentals in Chipley
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  • Enter your travel dates to view the best deals on holiday rentals in Chipley while they last

Look no further and take a look at our great range of rental properties in Chipley!

Frequently asked questions

Can I find holiday rentals in Chipley?

Yes, there are holiday rentals close to the most popular sights in Chipley, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Chipley has to offer?

Beach House - Sunset Paradise by PHG: This holiday home rental outside Chipley 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 such as a coffee maker and free parking are also available for your convenience.

How many holiday rentals are there in Chipley?

Choose from 7 Expedia holiday rentals in Chipley for a memorable holiday.

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 holiday rentals like in Chipley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chipley. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.