Charter Oaks Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿4,531 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Charter Oaks

Find the best Charter Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Charter Oaks
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

Top hotels in Charter Oaks

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
The price is ฿9,315 per night from 24 Mar to 25 Mar
฿9,315
฿11,786 total
24 Mar - 25 Mar
includes taxes & fees
9.4/10 Exceptional! (3,067 reviews)
Perfect view

Reviewed on 9 Mar 2026

Wyndham Grand Clearwater Beach
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is ฿9,997 per night from 11 Mar to 12 Mar
฿9,997
฿13,277 total
11 Mar - 12 Mar
includes taxes & fees
8.4/10 Very Good! (1,666 reviews)
Clean room nice upgrade

Reviewed on 9 Mar 2026

RumFish Beach at TradeWinds
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is ฿9,860 per night from 24 Mar to 25 Mar
฿9,860
฿12,402 total
24 Mar - 25 Mar
includes taxes & fees
8/10 Very Good! (2,490 reviews)
Loved the location!! Easy walk to shopping, dinner and the beach! We were very pleased with our stay! Would recommend it to all our friends!

Reviewed on 9 Mar 2026

Hilton Clearwater Beach Resort & Spa
See all 15,403 properties in Charter Oaks
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.

Frequently asked questions

How much does a Charter Oaks holiday package cost?
Custom make your Charter Oaks package from as little as . Choose from any combination of rental cars, flights and hotels to pull together the getaway you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to Charter Oaks?
By bundling. Hotels, rental cars and flights — combine whatever you need into a Charter Oaks holiday package to save a ton of cash. Score even more discounts when you include extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your trip your own way. We offer more than 550 airlines and 1,000,000 hotels worldwide, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Charter Oaks?
A holiday in Charter Oaks isn't complete without stopping by Eddie C. Moore Softball Complex, Westfield Countryside Mall and Bright House Field. Spend your evenings close to these popular attractions and make sightseeing a breeze.
How far in advance should I book my Charter Oaks holiday?
Your safest bet is to book early. Air carriers generally advertise flight tickets around a year ahead of departure, and this is an excellent opportunity to pick up some of the cheapest prices. Boss just told you to take some holiday time in a few weeks? That's alright! Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Charter Oaks travel package include?
Flights, hotels and rental cars, or any combination of the three — the choice is all yours! Whether you're visiting Charter Oaks with the kids or travelling solo, there's a bundle to fit every style and budget. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Charter Oaks travel package?
When you book your flights, hotels and car rentals together, you'll score incredible discounts. Whether you're organising a mountain getaway in a cabin or prefer to stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Charter Oaks Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines worldwide, so you have options galore when organising your Charter Oaks adventure.
If I'm not able to travel, can I cancel my Charter Oaks holiday package?
Don't stress if you're rethinking your Charter Oaks holiday package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally understand your circumstances can suddenly change, so head to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

Popular places to visit

Florida. Madeira Beach Florida. Gulf of Mexico or ocean beach, Hotels and Resorts. John's Pass Village and Boardwalk. Turquoise color of salt water. American shore. Summer or Autumn vacation.

John's Pass Village & Boardwalk

4/5(33 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area or visit its top-notch restaurants.

John's Pass Village & Boardwalk
Eckerd College which includes a garden

Eckerd College

Walk around the campus at Eckerd College as part of your travels around St. Petersburg. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Eckerd College
StPetersburg_JannusLive_553248621533125382_02

Jannus Live

Jannus Live is just one of the places to see in St. Petersburg, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Jannus Live

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

฿1,153
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

฿1,149
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

฿1,395
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.