Charter Oaks Holidays

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    Save up to €900 when you book a flight and hotel together*

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

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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
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area
5/5(3 area reviews)

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Top hotels in Charter Oaks

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is €302 per night from 31 May to 1 Jun
€302
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (3,239 reviews)
Didn’t like the water pressure. Every thing else was fine.

Reviewed on 16 May 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is €165 per night from 31 May to 1 Jun
€165
31 May - 1 Jun
includes taxes & fees
8.6/10 Excellent! (1,302 reviews)
Pool was closed. You are obligated to pay for parking, you choose between $35 for valet or $27 self park per day. Front desk advised it is $27 per day, in which resets at midnight, therefore for one overnight stay self park will cost you $54. I booked a room with full bay view, high floor. Little ...

Reviewed on 16 May 2026

The Westin Tampa Bay
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 €198 per night from 25 May to 26 May
€198
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,617 reviews)
It has been our third time at the Hilton in Clearwater. The service, food, and location were exceptional. We will definitely be back

Reviewed on 16 May 2026

Hilton Clearwater Beach Resort & Spa
See all 15,819 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

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

4.5/5(34 reviews)

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

John's Pass Village & Boardwalk
Fort De Soto Park

Fort De Soto Park

4.5/5(25 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park
Vinoy Park

Vinoy Park

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

€32
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

€38
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

€34
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.