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Holiday Rentals in Chipley

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Our top choices for Chipley holiday rentals

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, (5 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is €208
includes taxes & fees
15 Jul - 16 Jul
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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 €162
includes taxes & fees
9 Aug - 10 Aug
Cozy Lakefront Airstream

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
The price is €168
includes taxes & fees
15 Jul - 16 Jul
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.6 out of 10, Exceptional, (29 reviews)
"Super clean and quiet. My cat was welcome to join us. The owner was easy to contact."
United States
Sharon
The price is €234
includes taxes & fees
16 Jul - 17 Jul
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Comfortable Family Retreat in Panama City

Comfortable Family Retreat in Panama City
Panama City
The price is €373
includes taxes & fees
13 Aug - 14 Aug
Comfortable Family Retreat in Panama City

Pelican's Nest - The Hideaway in Panama City

Pelican's Nest - The Hideaway in Panama City
Panama City
9.8 out of 10, Exceptional, (16 reviews)
"Great!"
United States
Richard
The price is €168
includes taxes & fees
22 Jul - 23 Jul
Pelican's Nest - The Hideaway in Panama City

Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
3.5 star property
Panama City Beach
The price is €605
includes taxes & fees
14 Aug - 15 Aug
Calypso Beach Resort Tower 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 €422
includes taxes & fees
12 Aug - 13 Aug
3BR Canal-front Home w/ Wifi & Boat Dock

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, (23 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

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 €255
includes taxes & fees
13 Aug - 14 Aug
Origin 0538- Studio - Breath Taking Gulf Views

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 €592
includes taxes & fees
2 Aug - 3 Aug
Family-friendly Beach Retreat w/ Pools, Hot Tub & Tennis

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,192 reviews)
"Super nice!! Family friendly! Great location!"
United States
Kennedy
The price is €230
includes taxes & fees
12 Aug - 13 Aug
Origin At Seahaven

Polynesian #104 Ground Level

Polynesian #104 Ground Level
Panama City Beach
8.6 out of 10, Excellent, (61 reviews)
"Great location and view! "
United States
kerri m.
The price is €238
includes taxes & fees
12 Aug - 13 Aug
Polynesian #104 Ground Level

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, (183 reviews)
"Great stay"
United States
John
The price is €654
includes taxes & fees
21 Jul - 22 Jul
Calypso Beach Resort by Panhandle Getaways

Chic Panama City Beach Condo w/ Pool & Gulf Views

Chic Panama City Beach Condo w/ Pool & Gulf Views
Panama City Beach
9.6 out of 10, Exceptional, (54 reviews)
"Amazing condo!!!!"
United States
Jennifer T.
Chic Panama City Beach Condo w/ Pool & Gulf Views

Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.0 out of 10, Wonderful, (30 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is €563
includes taxes & fees
15 Jul - 16 Jul
Calypso Tower 3 by Panhandle Getaways

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 €466
includes taxes & fees
13 Aug - 14 Aug
Splash Beach Resort by Book That Condo

Walk to Beach + Restaurants: PCB Resort Condo!

Walk to Beach + Restaurants: PCB Resort Condo!
3.0 star property
Panama City Beach
9.0 out of 10, Wonderful, (10 reviews)
"Thank you great experience with my stay."
United States
Vanessa
The price is €315
includes taxes & fees
1 Aug - 2 Aug
Walk to Beach + Restaurants: PCB Resort Condo!

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, (256 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
The price is €334
includes taxes & fees
9 Aug - 10 Aug
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

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, (183 reviews)
"Pet friendly. Clean room. "
United States
amanda l.
The price is €575
includes taxes & fees
9 Aug - 10 Aug
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

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, apart-hotels, 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 favorite 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 depends 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 €230 per night. Entering your travel dates in the search wizard you might find 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?

Margaritaville Resort | 6BR Beach Oasis | Pool: This holiday home rental outside of Chipley is located on the beach, and offers a private balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.