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$285
includes taxes & fees
21 May - 22 May
Cozy Lakefront Airstream

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$435
includes taxes & fees
31 May - 1 June
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

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$316
includes taxes & fees
26 May - 27 May
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

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, (176 reviews)
"Great stay"
United States
John
The price is NZ$1,156
includes taxes & fees
27 May - 28 May
Calypso Beach Resort by Panhandle Getaways

Calypso Resort and Towers by Book That Condo

Calypso Resort and Towers by Book That Condo
4.0 star property
Panama City Beach
9.4 out of 10, Exceptional, (8 reviews)
"Perfect location"
United States
Weylin
The price is NZ$1,673
includes taxes & fees
5 June - 6 June
Calypso Resort and Towers by Book That Condo

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, (27 reviews)
"Amazing place"
United States
Alex R.
The price is NZ$442
includes taxes & fees
26 May - 27 May
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Beach House - The Sanderling by PHG

Beach House - The Sanderling by PHG
4.0 star property
Sunnyside
The price is NZ$2,044
includes taxes & fees
22 May - 23 May
Beach House - The Sanderling by PHG

Origin At Seahaven

Origin At Seahaven
3.5 star property
Panama City Beach
7.0 out of 10, Good, (2,185 reviews)
"Kitchen was fully equipped, everything we needed and like a 5 minute walk from the beach access"
United States
Leigha
The price is NZ$417
includes taxes & fees
21 May - 22 May
Origin At Seahaven

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 NZ$731
includes taxes & fees
21 May - 22 May
Beautiful PCB Townhome: Balcony & Resort Amenities

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, (250 reviews)
"Great stay while in town for baseball. "
United States
Jessica T.
The price is NZ$668
includes taxes & fees
3 June - 4 June
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

BEACHFRONT GRAND PANAMA, 1ST FLR DIRECT to BEACH/HEATED POOLS/SMART TV/FREE WIFI

BEACHFRONT GRAND PANAMA, 1ST FLR DIRECT to BEACH/HEATED POOLS/SMART TV/FREE WIFI
Panama City Beach
10.0 out of 10, Exceptional, (171 reviews)
"Great place, I will stay here again. "
United States
Darla H.
BEACHFRONT GRAND PANAMA, 1ST FLR DIRECT to BEACH/HEATED POOLS/SMART TV/FREE WIFI

June Specials - Oceanfront Condo, Large Balcony!

June Specials - Oceanfront Condo, Large Balcony!
Panama City Beach
9.6 out of 10, Exceptional, (62 reviews)
"View of ocean kitchen was great "
United States
Gregory W T.
The price is NZ$1,222
includes taxes & fees
19 June - 20 June
June Specials - Oceanfront Condo, Large Balcony!

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 NZ$970
includes taxes & fees
29 May - 30 May
Sterling Breeze by Panhandle Getaways

14th Floor Condo with Beautiful Views! Summer Deals!! Free Activities!

14th Floor Condo with Beautiful Views! Summer Deals!! Free Activities!
Panama City Beach
9.6 out of 10, Exceptional, (90 reviews)
"We had an awesome stay the room and building grounds where very well taken care of and everyone was very pleasant "
United States
Lisa W.
The price is NZ$1,407
includes taxes & fees
21 May - 22 May
14th Floor Condo with Beautiful Views! Summer Deals!! Free Activities!

Grand Panama Beach Resort by Book That Condo

Grand Panama Beach Resort by Book That Condo
4.0 star property
Panama City Beach
9.0 out of 10, Wonderful, (42 reviews)
"I was moved by book that condo to boardwalk beach redort"
United States
Jennifer
The price is NZ$1,574
includes taxes & fees
29 May - 30 May
Grand Panama Beach Resort by Book That Condo

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, (23 reviews)
"excellent location - very clean and fun pool area "
United States
Dave
The price is NZ$1,090
includes taxes & fees
26 May - 27 May
Calypso Tower 3 by Panhandle Getaways

JULY is OPEN! Tidewater 1ST FLOOR 2Br BEACHFRONT 2-Level Condo, Pools, Pier Park

JULY is OPEN! Tidewater 1ST FLOOR 2Br BEACHFRONT 2-Level Condo, Pools, Pier Park
Panama City Beach
10.0 out of 10, Exceptional, (127 reviews)
"Very accommodating, and all staff are so courteous. "
United States
Caroline M.
The price is NZ$841
includes taxes & fees
3 June - 4 June
JULY is OPEN! Tidewater 1ST FLOOR 2Br BEACHFRONT 2-Level Condo, Pools, Pier Park

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.
Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf 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 NZ$924
includes taxes & fees
7 June - 8 June
3BR Canal-front Home w/ Wifi & Boat Dock

Luxury Beachfront Condo Sleeps 6 Resort Pool Next to Pier

Luxury Beachfront Condo Sleeps 6 Resort Pool Next to Pier
Panama City Beach
9.8 out of 10, Exceptional, (131 reviews)
"ALWAYS the most enjoyable experience with Dawn's Rentals at Reef Memories! See ya at the beach next time!"
United States
Beverly T.
The price is NZ$1,023
includes taxes & fees
10 June - 11 June
Luxury Beachfront Condo Sleeps 6 Resort Pool Next to Pier
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$534 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.