Chipley Holiday Rentals

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Our top choices for Chipley holiday rentals

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$235
includes taxes & fees
3 May - 4 May
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 AU$231
includes taxes & fees
29 Apr - 30 Apr
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

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, (3 reviews)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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, (25 reviews)
"Amazing place"
United States
Alex R.
The price is AU$360
includes taxes & fees
29 Apr - 30 Apr
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

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, (175 reviews)
"Stayed for the local Ironman event. Perfect location for the event. We really enjoyed our stay and would recommend!"
United States
Peter
The price is AU$854
includes taxes & fees
22 Apr - 23 Apr
Calypso Beach Resort by Panhandle Getaways

Beautiful Beach House

Beautiful Beach House
Panama City
9.4 out of 10, Exceptional, (51 reviews)
"We had a great stay. Property is very nice and plenty of room for our group. Location is within driving distance of many things we wanted to do during our stay."
United States
Karon P.
Beautiful Beach House

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)
"Very nice place to stay."
United States
Howard L.
The price is AU$262
includes taxes & fees
22 Apr - 23 Apr
Pelican's Nest - The Hideaway in Panama City

Grand Panama Beach Resort

Grand Panama Beach Resort
4.0 star property
Panama City Beach
6.4 out of 10, (5 reviews)
"Nice!"
United States
Erik
The price is AU$707
includes taxes & fees
28 Apr - 29 Apr
Grand Panama Beach Resort

Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf Resort Tower 1

Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf Resort Tower 1
Panama City Beach
10.0 out of 10, Exceptional, (71 reviews)
"Excellent vacation"
United States
Brittany H.
The price is AU$994
includes taxes & fees
22 Apr - 23 Apr
Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf Resort Tower 1

Private Cozy bedroom with on suite living room

Private Cozy bedroom with on suite living room
Panama City
9.8 out of 10, Exceptional, (29 reviews)
"According to our friends the stay was very peaceful and very relaxing for them."
United States
Ken N.
The price is AU$195
includes taxes & fees
2 May - 3 May
Private Cozy bedroom with on suite living room

BEACHFRONT CONDO NOW ACCEPTING RENTALS!!

BEACHFRONT CONDO NOW ACCEPTING RENTALS!!
Panama City Beach
9.2 out of 10, Wonderful, (124 reviews)
"Great location, beautiful balcony view, and my kids loved the bunk beds! Would definitely stay here again!"
United States
Kathy W.
The price is AU$681
includes taxes & fees
27 Apr - 28 Apr
BEACHFRONT CONDO NOW ACCEPTING RENTALS!!

Tidewater - Breathtaking first-line beach views! Walking distance to Pier Park

Tidewater - Breathtaking first-line beach views! Walking distance to Pier Park
Panama City Beach
9.6 out of 10, Exceptional, (25 reviews)
"Our stay at Tidewater was amazing. We enjoyed the numerous amenities on the property, as well as our daily beach walks. The location of this property was perfect for us. This particular unit was spacious, clean and comfortable and we look forward to staying here again. "
United States
Susan
Tidewater - Breathtaking first-line beach views! Walking distance to Pier Park

Newly renovated! Two kings and bunks!Welcome to Paradise! Luxury Beach Front!

Newly renovated! Two kings and bunks!Welcome to Paradise! Luxury Beach Front!
Panama City Beach
9.8 out of 10, Exceptional, (45 reviews)
"We had a great time while staying here. The condo is beautiful and well equipped. We will definitely stay here again. "
United States
Nichole F.
The price is AU$990
includes taxes & fees
26 Apr - 27 Apr
Newly renovated! Two kings and bunks!Welcome to Paradise! Luxury Beach Front!

Summer Deals!! Amazing Updated Condo on the 21st Floor! Free Activities!

Summer Deals!! Amazing Updated Condo on the 21st Floor! Free Activities!
Panama City Beach
9.6 out of 10, Exceptional, (114 reviews)
"We were in PCB for a baseball tournament. We loved our condo, my grandson (15) went to the beach or the hot tub everyday. There was plenty of room for the 3 of us. We watched the fireworks at midnight 1-1-26 from our balcony. We would definitely recommend it to friends and family!!"
United States
Cathy S.
Summer Deals!! Amazing Updated Condo on the 21st Floor! Free Activities!

Grand Panama Beach Resort by Panhandle Getaways

Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.6 out of 10, Excellent, (104 reviews)
"Location was great"
United States
Tariq
The price is AU$1,008
includes taxes & fees
10 May - 11 May
Grand Panama Beach Resort 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 AU$997
includes taxes & fees
22 Apr - 23 Apr
Splash Beach Resort by Book That Condo

Corner Condo - Stunning Gulf Views -Comp. Beach Service, Water Park & Lazy River

Corner Condo - Stunning Gulf Views -Comp. Beach Service, Water Park & Lazy River
Panama City Beach
9.8 out of 10, Exceptional, (221 reviews)
"We loved our stay. We had a nice large balcony, easy access to the pool, splash pad, and beach. "
United States
Courtney C.
The price is AU$885
includes taxes & fees
28 Apr - 29 Apr
Corner Condo - Stunning Gulf Views -Comp. Beach Service, Water Park & Lazy River

Beach chairs included! Summer will be here soon!

Beach chairs included! Summer will be here soon!
Panama City Beach
10.0 out of 10, Exceptional, (202 reviews)
"Best kitchen in a condo I’ve stayed in. Great place. "
United States
Phillip G.
The price is AU$794
includes taxes & fees
19 May - 20 May
Beach chairs included! Summer will be here soon!

#101 Somerset PETS WELCOMED

#101 Somerset PETS WELCOMED
Bahama Beach
8.4 out of 10, Very good, (21 reviews)
"Very clean and a great price for the location!"
United States
Matthew
The price is AU$380
includes taxes & fees
4 May - 5 May
#101 Somerset PETS WELCOMED

Luxury Beachfront Westend Townhome - 4 Ensuite Bedrooms w Pool

Luxury Beachfront Westend Townhome - 4 Ensuite Bedrooms w Pool
Panama City Beach
10.0 out of 10, Exceptional, (91 reviews)
"Great Host"
United States
wayne l.
Luxury Beachfront Westend Townhome - 4 Ensuite Bedrooms w Pool
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$392 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?

Beachfront Luxury! 4BR Townhouse w/Pool & Stunning Gulf Views! Sleeps 10!: This holiday home rental outside of Chipley is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 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 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. In the wider area, you’ll find Pal's Park and Moss Hill Methodist Church.

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.