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

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chipley holiday rentals

House (3 Bedrooms) | Interior

1. 3BR Canal-front Home w/ Wifi & Boat Dock

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
The price is 3.285.450 ₫
12.560.067 ₫ total
includes taxes & fees
15 Aug - 16 Aug
3BR Canal-front Home w/ Wifi & Boat Dock
Condo, 3 Bedrooms, Ocean View (1708E) | View from room

2. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (3 reviews)
"Goo"
United States
Mario
The price is 3.911.250 ₫
15.131.469 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Calypso Beach Resort Tower 1
Condo, 3 Bedrooms, Sea View (2302W) | View from room

3. Calypso Beach Resort by Panhandle Getaways

Calypso Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (188 reviews)
"Great summer vacation choice!"
United States
Christina
The price is 4.172.000 ₫
16.961.433 ₫ total
includes taxes & fees
16 Aug - 17 Aug
Calypso Beach Resort by Panhandle Getaways
2 Bedroom Gulf View | Living area | 50-inch flat-screen TV with cable channels, TV

4. Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,201 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
The price is 2.138.150 ₫
6.347.548 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Origin At Seahaven
Indoor pool, 2 outdoor pools

5. Splash Beach Resort by Book That Condo

Splash Beach Resort by Book That Condo
4.0 star property
Panama City Beach
9.4 out of 10, Exceptional, (16 reviews)
"Love the family vibes."
United States
Ashley
Splash Beach Resort by Book That Condo
On the beach, white sand

6. 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, (36 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is 3.490.399 ₫
16.219.901 ₫ total
includes taxes & fees
18 Aug - 19 Aug
Calypso Tower 3 by Panhandle Getaways
Beach nearby

7. Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis
3.5 star property
Panama City Beach
The price is 2.831.224 ₫
15.668.597 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis
Condo, 1 Bedroom, Beachfront (2210) | Balcony

8. Aqua Beach Resort by Panhandle Getaways

Aqua Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
Justin
Aqua Beach Resort by Panhandle Getaways
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

Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

10/10 Excellent
"Very good location very nice rooms -"
Ray 2-night trip
Posted 1 hour ago
Chateau Beachfront Hotel, A By The Sea Resort

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.

How many holiday rentals are there in Chipley?

Choose from 6 Expedia holiday rentals in Chipley for a memorable holiday.

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. Pal's Park 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.