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 NZ$300
includes taxes & fees
7 Apr - 8 Apr
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 NZ$286
includes taxes & fees
14 Apr - 15 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.
The price is NZ$367
includes taxes & fees
6 Apr - 7 Apr
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Private Cozy bedroom with on suite living room

Private Cozy bedroom with on suite living room
Panama City
9.8 out of 10, Exceptional, (28 reviews)
"According to our friends the stay was very peaceful and very relaxing for them."
United States
Ken N.
The price is NZ$260
includes taxes & fees
29 Apr - 30 Apr
Private Cozy bedroom with on suite living room

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 NZ$451
includes taxes & fees
5 Apr - 6 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, (170 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 NZ$1,136
includes taxes & fees
27 Apr - 28 Apr
Calypso Beach Resort by Panhandle Getaways

Pelican's Nest - The Hideaway in Panama City

Pelican's Nest - The Hideaway in Panama City
Panama City
9.8 out of 10, Exceptional, (14 reviews)
"Very nice place to stay."
United States
Howard L.
The price is NZ$327
includes taxes & fees
9 Apr - 10 Apr
Pelican's Nest - The Hideaway in Panama City

Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (21 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is NZ$1,030
includes taxes & fees
12 Apr - 13 Apr
Calypso Tower 3 by Panhandle Getaways

Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.4 out of 10, Exceptional, (11 reviews)
"Room was typical of a hotel stlye room. Wish there was a place to put clothes and a place for soap/wash cloth etc in the shower. Full sized refrigerator was nice to hold all of our families food stuffs. View was spectacular. No heated pool or hot tub but id imagine during the warmer season that doesnt matter."
United States
herbert
The price is NZ$448
includes taxes & fees
5 Apr - 6 Apr
Newly renovated studio on the beach # 304

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
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is NZ$726
includes taxes & fees
5 Apr - 6 Apr
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.4 out of 10, Exceptional, (117 reviews)
"The views were Amazing ..My quate little condo was just the right size for myself n my guests .. definitely will recommend for a little getaway for 2"
United States
Deanna
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

#101 Somerset PETS WELCOMED

#101 Somerset PETS WELCOMED
Bahama Beach
8.4 out of 10, Very good, (20 reviews)
"Very clean and a great price for the location!"
United States
Matthew
The price is NZ$473
includes taxes & fees
4 May - 5 May
#101 Somerset PETS WELCOMED

~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (52 reviews)
"Very clean and comfortable. Would definitely recommend for a family."
United States
Neil L.
The price is NZ$722
includes taxes & fees
12 Apr - 13 Apr
~ La Conchita ~ w private pool & Firepit

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 NZ$1,199
includes taxes & fees
22 Apr - 23 Apr
Splash Beach Resort by Book That Condo

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 NZ$868
includes taxes & fees
14 Apr - 15 Apr
Grand Panama Beach Resort

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, (204 reviews)
"Perfect for families especially with small children. Amazing view! Perfect location! Will stay again! "
United States
Sabrina
The price is NZ$942
includes taxes & fees
8 Apr - 9 Apr
Splash Beach Resort by Panhandle Getaways

Origin 1333 - Studio - Amazing Value - Gulf Views

Origin 1333 - Studio - Amazing Value - Gulf Views
Panama City Beach
9.4 out of 10, Exceptional, (52 reviews)
"Great location and amenities. "
United States
Brian W.
The price is NZ$513
includes taxes & fees
7 Apr - 8 Apr
Origin 1333 - Studio - Amazing Value - Gulf Views

4th Floor! ☼☼❀❀ 2BR/2BA,Sleeps 7,Handicap Acc,Living & Mstr Rms Facing The Beach

4th Floor! ☼☼❀❀ 2BR/2BA,Sleeps 7,Handicap Acc,Living & Mstr Rms Facing The Beach
Panama City
9.4 out of 10, Exceptional, (205 reviews)
"The host was very welcoming. We had a very peaceful and relaxing Thanksgiving! "
United States
Joseph V.
The price is NZ$660
includes taxes & fees
4 May - 5 May
4th Floor! ☼☼❀❀ 2BR/2BA,Sleeps 7,Handicap Acc,Living & Mstr Rms Facing The Beach

3BR Canal-front Home w/ Wifi & Boat Dock

3BR Canal-front Home w/ Wifi & Boat Dock
3.0 star property
Bayside Park
3BR Canal-front Home w/ Wifi & Boat Dock

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 NZ$860
includes taxes & fees
14 Apr - 15 Apr
BEACHFRONT CONDO NOW ACCEPTING RENTALS!!
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 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 NZ$409 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?

OCEAN FRONT / ON THE BEACH Charming Townhome at West Side of PCB- LAGUNA BEACH: This holiday home rental outside of Chipley is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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. 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.