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Chipley Holiday Rentals

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Our top choices for Chipley holiday 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 AU$206
includes taxes & fees
8 Sept - 9 Sept
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 AU$234
includes taxes & fees
7 Sept - 8 Sept
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)
"Great place to stay!"
United States
Carrie P.
The price is AU$340
includes taxes & fees
7 Sept - 8 Sept
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 AU$359
includes taxes & fees
18 Sept - 19 Sept
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.
~ 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 AU$862
includes taxes & fees
14 Sept - 15 Sept
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 AU$787
includes taxes & fees
10 Sept - 11 Sept
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 AU$430
includes taxes & fees
2 Oct - 3 Oct
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 AU$498
includes taxes & fees
16 Sept - 17 Sept
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 AU$680
includes taxes & fees
9 Sept - 10 Sept
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 AU$813
includes taxes & fees
7 Sept - 8 Sept
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 AU$676
includes taxes & fees
7 Sept - 8 Sept
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 AU$737
includes taxes & fees
7 Sept - 8 Sept
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 AU$552
includes taxes & fees
15 Sept - 16 Sept
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.
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 AU$756
includes taxes & fees
7 Sept - 8 Sept
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 AU$434
includes taxes & fees
7 Sept - 8 Sept
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 AU$476
includes taxes & fees
20 Sept - 21 Sept
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 AU$480
includes taxes & fees
7 Sept - 8 Sept
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 AU$421
includes taxes & fees
6 Sept - 7 Sept
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.
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Top Chipley Hotel Reviews

Find out more about Chipley

Everything you need to know about Chipley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chipley holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chipley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley holiday rentals we have selected for you start as low as AU$620 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley holiday 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 holiday.

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. 

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 of 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 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.