A waterfall cascading over a rocky cliff surrounded by lush green ferns and foliage.

Chipley Holiday Rentals

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Our top choices for Chipley holiday rentals

1. The Cozy Farmhouse Retreat

The Cozy Farmhouse Retreat
Chipley
The price is NZ$785
includes taxes & fees
17 Oct - 18 Oct
The Cozy Farmhouse Retreat

2. 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
10.0 out of 10, Exceptional, (1 review)
"Very nice place to stay. Host was very helpful and accommodating. Enjoyed being way out in the country."
United States
Gwen S.
The price is NZ$269
includes taxes & fees
19 Oct - 20 Oct
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

3. Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Carrie P.
The price is NZ$423
includes taxes & fees
17 Oct - 18 Oct
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

4. 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$322
includes taxes & fees
2 Nov - 3 Nov
Cozy Lakefront Airstream

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

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.8 out of 10, Exceptional, (36 reviews)
"Amazing place"
United States
Alex R.
The price is NZ$459
includes taxes & fees
17 Oct - 18 Oct
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

6. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (56 reviews)
"Great location!Kids loved the pool even if it was cold. The owners were amazing, and quick to respond."
United States
Ellen D.
~ La Conchita ~ w private pool & Firepit

7. Calypso Beach Resort Tower 2 by Panhandle Getaways

Calypso Beach Resort Tower 2 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (196 reviews)
"The room and view were absolutely amazing!"
United States
Brittany
The price is NZ$1,109
includes taxes & fees
18 Oct - 19 Oct
Calypso Beach Resort Tower 2 by Panhandle Getaways

8. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Panama City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and unique hidden gem of panama city, it may be in the city but you cant tell while at the house. Its extremely private and secluded, wildlife was everywhere, we watch herons and ducks in the bayou behind the house, a fox and a family of possums in the back yard after dusk. Its dog friendly and close to a lot of dog friendly restaurants, it also has a kayak launch and the fishing is incredible in the bayou. We caught multiple trout and reddish. Ill be posting a video on youtube @...
United States
William
The price is NZ$549
includes taxes & fees
19 Oct - 20 Oct
Private - Waterfront Cottage - Panama City, FL

9. 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, (31 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!

10. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (14 reviews)
"My wife and I loved that everything was close by. Qill definitely stay again 10/10"
United States
shawn
The price is NZ$1,464
includes taxes & fees
24 Oct - 25 Oct
Calypso Beach Resort Tower 1

11. Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (41 reviews)
"The property was very clean and in an excellent location . We weren’t on the beach , but we had a great view of the ocean and the pools I would highly recommend"
United States
Thomas
The price is NZ$1,755
includes taxes & fees
17 Oct - 18 Oct
Calypso Tower 3 by Panhandle Getaways

12. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
The price is NZ$628
includes taxes & fees
17 Oct - 18 Oct
Octa Collection on Front Beach

13. 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 NZ$474
includes taxes & fees
29 Oct - 30 Oct
Origin 0538- Studio - Breath Taking Gulf Views

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

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.6 out of 10, Exceptional, (137 reviews)
"Great little place to stay and the views were nice!"
United States
Andres
The price is NZ$329
includes taxes & fees
10 Nov - 11 Nov
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

15. Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.4 out of 10, Exceptional, (24 reviews)
"The room was clean and had everything we needed for our stay. The view from the front door of the beach was beautiful! I would stay with them again!"
United States
Whitney F.
The price is NZ$696
includes taxes & fees
2 Nov - 3 Nov
Newly renovated studio on the beach # 304

16. Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!
Panama City Beach
9.8 out of 10, Exceptional, (139 reviews)
"Great stay."
United States
John S.
The price is NZ$788
includes taxes & fees
21 Oct - 22 Oct
Magnificent View of the Gulf of America Near Pier Park. BOOK YOUR VACATION NOW!

17. Emerald Beach Resort by Panhandle Getaways

Emerald Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
8.6 out of 10, Excellent, (29 reviews)
"Everything was perfect. Really good experience "
United States
Senad
The price is NZ$1,035
includes taxes & fees
18 Oct - 19 Oct
Emerald Beach Resort by Panhandle Getaways

18. Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!

Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!
Panama City Beach
9.6 out of 10, Exceptional, (12 reviews)
"Excellent location to and the complimentary two beach chairs and beach umbrella was amazing."
United States
Paulo
The price is NZ$597
includes taxes & fees
25 Oct - 26 Oct
Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!

19. Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!

Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!
Panama City Beach
9.2 out of 10, Wonderful, (187 reviews)
"This was an amazing stay for my daughter’s spring break. We did have an issue with the door not locking, and the team was quick to come resolve the issue. Would def stay here again!"
United States
Amber B.
The price is NZ$1,039
includes taxes & fees
21 Oct - 22 Oct
Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!

20. Ocean view from the 13th Floor. Owner Operated.

Ocean view from the 13th Floor. Owner Operated.
Panama City Beach
9.8 out of 10, Exceptional, (277 reviews)
"Had an incredible time. It was the perfect place to stay with my family."
United States
Kelli
The price is NZ$553
includes taxes & fees
2 Nov - 3 Nov
Ocean view from the 13th Floor. Owner Operated.
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$339 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?

Beach House - Sunset Paradise by PHG: This holiday home rental outside Chipley is located by the ocean, and offers a private balcony, air conditioning and Netflix to help you feel perfectly comfortable in your new surroundings. Amenities such as a coffee maker and free parking are also available for your convenience.

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 Pal's Park are a couple of lovely local spots to get outside and enjoy nature. Lucas Lake 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.