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Chipley Vacation Rentals

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Our top choices for Chipley vacation rentals

1. The Cozy Farmhouse Retreat

The Cozy Farmhouse Retreat
Chipley
The price is CA $305
CA $645 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $118
CA $214 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $172
CA $339 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $159
CA $235 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $226
CA $405 total
includes taxes & fees
Oct 20 - Oct 21
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)
"The house was amazing. We really enjoyed our stay and it was in a great location. Would definitely stay again."
United States
Jordan B.
The price is CA $127
CA $518 total
includes taxes & fees
Oct 28 - Oct 29
~ 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 CA $176
CA $863 total
includes taxes & fees
Oct 20 - Oct 21
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)
"Beautiful home in a quiet space by the canal. My husband, daughters , dog and I loved staying there. It was clean and well maintained. We were close enough to the beach and shopping for daily trips for activities! Very pleased with the stay and our very friendly and easy to communicate with host! Highly recommend!"
United States
Andrea J.
The price is CA $153
CA $421 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is CA $126
CA $520 total
includes taxes & fees
Oct 20 - Oct 21
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, (15 reviews)
"Beautiful view. convenient location"
United States
Tien
The price is CA $176
CA $779 total
includes taxes & fees
Oct 21 - Oct 22
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, (42 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 CA $97
CA $758 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $204
CA $494 total
includes taxes & fees
Nov 18 - Nov 19
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 CA $100
CA $421 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $106
CA $262 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $132
CA $529 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $126
CA $564 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $189
CA $852 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $107
CA $486 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $215
CA $829 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $141
CA $451 total
includes taxes & fees
Oct 26 - Oct 27
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chipley vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley vacation rentals we have selected for you start as low as CA $268 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 vacation 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 vacation.

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 vacation rentals in Chipley?

Yes, there are vacation rentals close to popular points of interest in Chipley, or you can go with a secluded option if you'd like a relaxing place to 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's the top vacation rental that Chipley has to offer?

Beach House - Sunset Paradise by PHG: You might want to consider this Chipley vacation home rental for your stay. It 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 like a coffee maker and free parking are also available for your convenience.

How many vacation rentals are there in Chipley?

Choose from 6 Expedia vacation rentals in Chipley for a memorable vacation.

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 vacation rentals like in Chipley?

Vacation rentals are private accommodations you can book for a couple days or more in Chipley. Vacation rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.