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Holiday Rentals in Chipley

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Our top choices for Chipley holiday rentals

1. 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 €147
includes taxes & fees
30 Aug - 31 Aug
Cozy Lakefront Airstream

2. 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, (6 reviews)
The price is €208
includes taxes & fees
30 Aug - 31 Aug
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

3. 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 €129
includes taxes & fees
14 Sept - 15 Sept
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

4. 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, (35 reviews)
"Amazing place"
United States
Alex R.
The price is €229
includes taxes & fees
30 Aug - 31 Aug
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

5. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (55 reviews)
"Great location!Kids loved the pool even if it was cold. The owners were amazing, and quick to respond."
United States
Ellen D.
The price is €373
includes taxes & fees
1 Sept - 2 Sept
~ La Conchita ~ w private pool & Firepit

6. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (19 reviews)
"Perfect stay "
United States
Jess C.
The price is €257
includes taxes & fees
29 Aug - 30 Aug
Private - Waterfront Cottage - Panama City, FL

7. 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
8.8 out of 10, Excellent, (26 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is €315
includes taxes & fees
29 Aug - 30 Aug
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

8. Studio Home Just a Minute Walk from the Beach! Book before gone!

Studio Home Just a Minute Walk from the Beach! Book before gone!
Panama City Beach
9.2 out of 10, Wonderful, (23 reviews)
"Just a nice place to stay while in Pcb."
United States
Benjamin P.
The price is €233
includes taxes & fees
29 Aug - 30 Aug
Studio Home Just a Minute Walk from the Beach! Book before gone!

9. Laguna Beach Condo with Gulf Views and Pool

Laguna Beach Condo with Gulf Views and Pool
Laguna Beach
9.8 out of 10, Exceptional, (31 reviews)
"Great stay! Peaceful and quiet location, but close to everything."
United States
Rachel M.
The price is €313
includes taxes & fees
1 Sept - 2 Sept
Laguna Beach Condo with Gulf Views and Pool

10. 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, (261 reviews)
"Nice stay"
United States
Dana M.
The price is €255
includes taxes & fees
30 Aug - 31 Aug
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

11. 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, (188 reviews)
"The only thing that I don’t like within our stay was how long we had to wait for elevators. The view and how peaceful it was was my favorite"
United States
Jeska R.
The price is €424
includes taxes & fees
2 Sept - 3 Sept
Exceptional Unit, Fantastic Gulf Views, Ceiling To Floor Windows,Pools!

12. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
10.0 out of 10, Exceptional, (4 reviews)
"Great place, we really enjoyed our trip and stay!"
United States
Brent
The price is €486
includes taxes & fees
10 Sept - 11 Sept
Calypso Beach Resort Tower 1

13. Coastal Breeze Perfect Family Getaway/ Sleep 9

Coastal Breeze Perfect Family Getaway/ Sleep 9
Laguna Beach
9.4 out of 10, Exceptional, (79 reviews)
"Property was easy to find. Very spacious. Plenty of room for our family. Great location in proximity to the beach, food, and shopping."
United States
Brittany K.
Coastal Breeze Perfect Family Getaway/ Sleep 9

14. 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, (185 reviews)
"We love staying at Grand Panama. Been there several times and it’s always wonderful."
United States
Nicole R.
The price is €460
includes taxes & fees
2 Sept - 3 Sept
Bring your Pet! Amazing 3rd floor unit! Outstanding Views and Amenities!

15. 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, (96 reviews)
"Very beautiful condo; we really enjoyed staying there even though it was a short visit!"
United States
Anonymous traveller
14th Floor Condo with Beautiful Views! Summer Deals!! Free Activities!

16. 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, (11 reviews)
"Excellent location to and the complimentary two beach chairs and beach umbrella was amazing."
United States
Paulo
The price is €304
includes taxes & fees
31 Aug - 1 Sept
Gulf-front Sunrise w/ Complimentary Beach Service + Attraction Tickets!

17. 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 €253
includes taxes & fees
28 Sept - 29 Sept
Origin 0538- Studio - Breath Taking Gulf Views

18. Beautiful Condo with beach view free beach service, wifi and 10% weekly discount

Beautiful Condo with beach view free beach service, wifi and 10% weekly discount
Panama City Beach
9.4 out of 10, Exceptional, (142 reviews)
"The kitschy had everything we could possibly need and more. The rooms were spacious and laid out perfectly for our needs. Beautiful view from balcony "
United States
Jim L.
Beautiful Condo with beach view free beach service, wifi and 10% weekly discount

19. 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, (274 reviews)
"Had an incredible time. It was the perfect place to stay with my family."
United States
Kelli
The price is €261
includes taxes & fees
7 Sept - 8 Sept
Ocean view from the 13th Floor.Owner Operated.

20. Large Deck/ in-law suite /Walk to Beach/ Location!

Large Deck/ in-law suite /Walk to Beach/ Location!
Panama City Beach
9.6 out of 10, Exceptional, (37 reviews)
"Great stay, host is amazing and always accommodating! Love staying here. "
United States
Leah N.
Large Deck/ in-law suite /Walk to Beach/ Location!
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 €383 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?

Tidal Charm by AvantStay | Walk to Beach, Community Pool, Balcony, Ocean Views: This holiday home rental outside of Chipley is located near the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchenette 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 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. Pal's Park 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.