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

Chipley Vacation Rentals

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Our top choices for Chipley vacation rentals

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 CA $124
CA $219 total
includes taxes & fees
Aug 12 - Aug 13
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

2. 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 CA $158
CA $233 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Lakefront Airstream

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

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
10.0 out of 10, Exceptional, (6 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is CA $170
CA $335 total
includes taxes & fees
Aug 9 - Aug 10
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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, (31 reviews)
"Super clean and quiet. My cat was welcome to join us. The owner was easy to contact."
United States
Sharon
The price is CA $210
CA $364 total
includes taxes & fees
Aug 20 - Aug 21
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

5. Comfortable Family Retreat in Panama City

Comfortable Family Retreat in Panama City
Panama City
The price is CA $224
CA $599 total
includes taxes & fees
Aug 16 - Aug 17
Comfortable Family Retreat in Panama City

6. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (55 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 CA $214
CA $628 total
includes taxes & fees
Sep 1 - Sep 2
~ La Conchita ~ w private pool & Firepit

7. 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 CA $177
CA $675 total
includes taxes & fees
Aug 15 - Aug 16
3BR Canal-front Home w/ Wifi & Boat Dock

8. Studio Home Just a Minute Walk from the Beach! Book before gone!

Studio Home Just a Minute Walk from the Beach! Book before gone!
Panama City Beach
9.0 out of 10, Wonderful, (22 reviews)
"Just a nice place to stay while in Pcb."
United States
Benjamin P.
The price is CA $116
CA $371 total
includes taxes & fees
Aug 31 - Sep 1
Studio Home Just a Minute Walk from the Beach! Book before gone!

9. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (2 reviews)
"Goo"
United States
Mario
The price is CA $194
CA $1,131 total
includes taxes & fees
Aug 15 - Aug 16
Calypso Beach Resort Tower 1

10. 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 CA $152
CA $842 total
includes taxes & fees
Aug 17 - Aug 18
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

11. Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,197 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
The price is CA $118
CA $345 total
includes taxes & fees
Sep 6 - Sep 7
Origin At Seahaven

12. Gulf Front Retreat with King Bed and Pool

Gulf Front Retreat with King Bed 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 CA $137
CA $551 total
includes taxes & fees
Aug 9 - Aug 10
Gulf Front Retreat with King Bed and Pool

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, (27 reviews)
"Everything was great!! The location was awesome!! We had a great time!!!"
United States
Jason W.
The price is CA $164
CA $645 total
includes taxes & fees
Aug 13 - Aug 14
Townhouse w/Gulf Views! Very Short walk to the Beach! Next to Pool!

14. Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
Panama City Beach
9.4 out of 10, Exceptional, (258 reviews)
"Every thing was what we saw in the advertisement. We would rent again."
United States
melinda h.
The price is CA $151
CA $459 total
includes taxes & fees
Aug 9 - Aug 10
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

15. 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, (186 reviews)
"Great summer vacation choice!"
United States
Christina
The price is CA $204
CA $977 total
includes taxes & fees
Aug 11 - Aug 12
Calypso Beach Resort by Panhandle Getaways

16. 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 CA $116
CA $405 total
includes taxes & fees
Aug 10 - Aug 11
Origin 0538- Studio - Breath Taking Gulf Views

17. 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
The price is CA $176
CA $678 total
includes taxes & fees
Aug 13 - Aug 14
Splash Beach Resort by Book That Condo

18. Coastal Breeze Perfect Family Getaway/ Sleep 9

Coastal Breeze Perfect Family Getaway/ Sleep 9
Laguna Beach
9.4 out of 10, Exceptional, (79 reviews)
"Property was easy to find. Very spacious. Plenty of room for our family. Great location in proximity to the beach, food, and shopping."
United States
Brittany K.
The price is CA $139
CA $485 total
includes taxes & fees
Sep 1 - Sep 2
Coastal Breeze Perfect Family Getaway/ Sleep 9

19. 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, (33 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is CA $204
CA $890 total
includes taxes & fees
Aug 8 - Aug 9
Calypso Tower 3 by Panhandle Getaways

20. 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
9.4 out of 10, Exceptional, (185 reviews)
"Pet friendly. Clean room. "
United States
amanda l.
The price is CA $137
CA $834 total
includes taxes & fees
Aug 11 - Aug 12
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!
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

Find out more about Chipley

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chipley. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 vacation home rental near Chipley, which 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 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 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.