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

Chipley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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 $109
CA $202 total
includes taxes & fees
Sep 8 - Sep 9
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 $155
CA $230 total
includes taxes & fees
Sep 9 - Sep 10
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 $169
CA $332 total
includes taxes & fees
Sep 7 - Sep 8
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, (35 reviews)
"Amazing place"
United States
Alex R.
The price is CA $207
CA $359 total
includes taxes & fees
Sep 7 - Sep 8
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

5. ~ 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 $125
CA $508 total
includes taxes & fees
Oct 1 - Oct 2
~ La Conchita ~ w private pool & Firepit

6. 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, (191 reviews)
"Great summer vacation choice!"
United States
Christina
The price is CA $156
CA $824 total
includes taxes & fees
Sep 5 - Sep 6
Calypso Beach Resort Tower 2 by Panhandle Getaways

7. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.0 out of 10, Wonderful, (7 reviews)
"The decor was nice and the rooms were clean also had a great view of the Gulf"
United States
Elijah
The price is CA $190
CA $782 total
includes taxes & fees
Sep 6 - Sep 7
Calypso Beach Resort Tower 1

8. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (19 reviews)
"Perfect stay "
United States
Jess C.
The price is CA $155
CA $413 total
includes taxes & fees
Sep 7 - Sep 8
Private - Waterfront Cottage - Panama City, FL

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
8.8 out of 10, Excellent, (27 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is CA $123
CA $509 total
includes taxes & fees
Sep 8 - Sep 9
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

10. 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, (17 reviews)
"The location, amenities, and room were clean and spacious. Elevators were quick and available."
United States
Ben
The price is CA $180
CA $675 total
includes taxes & fees
Sep 9 - Sep 10
Splash Beach Resort by Book That Condo

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, (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 CA $162
CA $815 total
includes taxes & fees
Sep 7 - Sep 8
Calypso Tower 3 by Panhandle Getaways

12. 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, (185 reviews)
"The only thing that I don’t like within our stay was how long we had to wait for elevators. The view and how peaceful it was was my favorite"
United States
Jeska R.
The price is CA $110
CA $683 total
includes taxes & fees
Sep 7 - Sep 8
Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!

13. Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza

Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza
Panama City Beach
9.4 out of 10, Exceptional, (154 reviews)
"We absolutely loved staying here. The condo was very nice and all the amenities on the property were amazing. The host was very responsive."
United States
Kelsey C.
The price is CA $160
CA $732 total
includes taxes & fees
Sep 7 - Sep 8
Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza

14. Laguna Beach Condo with Gulf Views and Pool

Laguna Beach Condo with Gulf Views 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 $136
CA $547 total
includes taxes & fees
Sep 13 - Sep 14
Laguna Beach Condo with Gulf Views and Pool

15. 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, (188 reviews)
"We love staying at Grand Panama. Been there several times and it’s always wonderful."
United States
Nicole R.
The price is CA $110
CA $752 total
includes taxes & fees
Sep 7 - Sep 8
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

16. Splash Beach Resort by Panhandle Getaways

Splash Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
7.4 out of 10, Good, (224 reviews)
"Great place to go with kids."
United States
Sohil
The price is CA $133
CA $751 total
includes taxes & fees
Sep 7 - Sep 8
Splash Beach Resort by Panhandle Getaways

17. 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, (273 reviews)
"Had an incredible time. It was the perfect place to stay with my family."
United States
Kelli
The price is CA $131
CA $431 total
includes taxes & fees
Sep 7 - Sep 8
Ocean view from the 13th Floor.Owner Operated.

18. Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.4 out of 10, Exceptional, (21 reviews)
"Great location! Right in the beach! Kinda in the middle of everything so you don’t have to travel very far either way you go!"
United States
Brandon t.
The price is CA $103
CA $484 total
includes taxes & fees
Sep 20 - Sep 21
Newly renovated studio on the beach # 304

19. 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 CA $109
CA $482 total
includes taxes & fees
Sep 7 - Sep 8
Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!

20. Gulf front Master Bedroom with Amazing View!

Gulf front Master Bedroom with Amazing View!
Panama City Beach
9.4 out of 10, Exceptional, (144 reviews)
"We had an amazing time at Panama City Beach. The unit was clean, well stocked and had an amazing view. This was our 2nd time staying here and it won't be our last."
United States
Rosa E.
The price is CA $130
CA $414 total
includes taxes & fees
Sep 6 - Sep 7
Gulf front Master Bedroom with Amazing View!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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.