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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 £125
includes taxes & fees
14 May - 15 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 £134
includes taxes & fees
12 May - 13 May
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 £190
includes taxes & fees
16 May - 17 May
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, (26 reviews)
"Amazing place"
United States
Alex R.
The price is £193
includes taxes & fees
12 May - 13 May
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

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)
"Overall great experience and would definitely stay again😊"
United States
Mary B.
The price is £104
includes taxes & fees
12 May - 13 May
Private Cozy bedroom with on suite living room

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 £139
includes taxes & fees
12 May - 13 May
Pelican's Nest - The Hideaway in Panama City

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, (181 reviews)
"Nice view. Good communication with escala host"
United States
Lori V.
The price is £385
includes taxes & fees
12 May - 13 May
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

#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 £200
includes taxes & fees
12 May - 13 May
#101 Somerset PETS WELCOMED

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 £352
includes taxes & fees
17 May - 18 May
3BR Canal-front Home w/ Wifi & Boat Dock

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, (105 reviews)
"Our room had a beach front view. The room was very clean and spacious. The bed slept great! We would definitely stay again. "
United States
Leslie
The price is £399
includes taxes & fees
12 May - 13 May
Grand Panama Beach Resort by Panhandle Getaways

🐾🏖️Summer Deals!! Free Activities for Summer ! DOG Friendly🏖️🐾

🐾🏖️Summer Deals!! Free Activities for Summer ! DOG Friendly🏖️🐾
Panama City Beach
9.4 out of 10, Exceptional, (32 reviews)
"The location was great. The access to the pool was awesome. Everything was in walking distance. The couch and chairs needs to be replaced and it had dog hair everywhere. "
United States
Bianca S.
The price is £439
includes taxes & fees
12 May - 13 May
🐾🏖️Summer Deals!! Free Activities for Summer ! DOG Friendly🏖️🐾

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, (119 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
The price is £158
includes taxes & fees
26 May - 27 May
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

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 £212
includes taxes & fees
17 May - 18 May
Origin 0538- Studio - Breath Taking Gulf Views

Overlooking the Gulf! Pools, Arcade + Free Beach Service & Attraction Tickets

Overlooking the Gulf! Pools, Arcade + Free Beach Service & Attraction Tickets
Panama City Beach
9.0 out of 10, Wonderful, (120 reviews)
"We had a very enjoyable stay"
United States
Robert F.
Overlooking the Gulf! Pools, Arcade + Free Beach Service & Attraction Tickets

Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!

Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!
Panama City Beach
9.8 out of 10, Exceptional, (264 reviews)
"Great stay!"
United States
Kathy E.
The price is £228
includes taxes & fees
12 May - 13 May
Book Now!! Balcony is right on the beachside. Great view of the Emerald Water!

BEACHFRONT!! FREE BEACH CHAIRS!! LOW 9TH FLOOR!! Over 146 Five Star Reviews!

BEACHFRONT!! FREE BEACH CHAIRS!! LOW 9TH FLOOR!! Over 146 Five Star Reviews!
Miramar Beach
10.0 out of 10, Exceptional, (185 reviews)
"The place was perfect and the view is so amazing! We loved our stay and the condo had everything we needed. Would absolutely stay again!"
United States
Tom M.
The price is £313
includes taxes & fees
12 May - 13 May
BEACHFRONT!! FREE BEACH CHAIRS!! LOW 9TH FLOOR!! Over 146 Five Star Reviews!

Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.6 out of 10, Exceptional, (15 reviews)
"Great value for being on the beach. Doesnt have a balcony but is right on the beach, pool is super close to the beach too"
United States
Dalton
The price is £252
includes taxes & fees
12 May - 13 May
Newly renovated studio on the beach # 304

Polynesian #104 Ground Level

Polynesian #104 Ground Level
Panama City Beach
8.8 out of 10, Excellent, (56 reviews)
"Our stay was exactly what we expected. A nice place to stay close to everything yet far enough away for the beech to no be too crowded. "
United States
heather h.
The price is £196
includes taxes & fees
26 May - 27 May
Polynesian #104 Ground Level

Beautiful PCB Townhome: Balcony & Resort Amenities

Beautiful PCB Townhome: Balcony & Resort Amenities
4.0 star property
Panama City Beach
10.0 out of 10, Exceptional, (2 reviews)
"Yes, everything was good and I like how the places to shop and eat were also close by."
United States
Ketline
The price is £329
includes taxes & fees
3 Jun - 4 Jun
Beautiful PCB Townhome: Balcony & Resort Amenities

Sterling Breeze by Panhandle Getaways

Sterling Breeze by Panhandle Getaways
3.5 star property
Panama City Beach
8.4 out of 10, Very good, (32 reviews)
"Not clean , had a water leak in the kitchen they fixed next day. No internet or WF that all, need your own WF or hotspot. Only 2 elevators in the building, pool it was ok but nothing else was offered that ice cream. For someone who called this resort …. Not resort they all. Just regular apartment building!"
United States
Slavica
The price is £352
includes taxes & fees
17 May - 18 May
Sterling Breeze by Panhandle Getaways
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 £196 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?

❃ Walkable to Food & Fun ❃ Beach-Front Pool ❃ Canal-Side Home ❃ No Pet Fee: This holiday home rental outside of Chipley is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.