Charter Oaks Vacation Packages

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Top Holiday Package Deals in Charter Oaks

Price found within the past 48 hours. Click for updated prices.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
7.6/10 Good! (1,005 reviews)
Completely remodeled- looks great!

Reviewed on Jun. 1, 2024

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,004 reviews)
Beautiful grounds. Rooms were clean and spacious. Would stay here again

Reviewed on May 29, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug. 7 - Aug. 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tampa (TPA)
9.6/10 Exceptional! (297 reviews)
The property was really nice. It was across the street a park that the up-keeping was not that great.

Reviewed on May 27, 2024

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,244 reviews)
We had a maintenance issue with the toilet continuously running and the tech came and changed the toilet assembly incorrectly with problem not being resolved. He also did not return the toilet tank cover back on the toilet properly and it was hanging off the side of the toilet. When we arrived there was trash on the common area floors and the trash can near the elevator was overflowing. We checked out 4 days later and the same trash was on the floor and the trash can was still overflowing.

Reviewed on Jun. 3, 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul. 21 - Jul. 27
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (1,001 reviews)
Lively motel with great location and access to the beach. Friendly staff. Kitchenette is great convenience. Would stay again.

Reviewed on Jun. 2, 2024

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

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotel + flight trips in Pass-a-Grille

Charter Oaks Hotel Deals

RumFish Beach Resort by TradeWinds
RumFish Beach Resort by TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jun. 5 to Jun. 6
CA $232
CA $347 total
includes taxes & fees
Jun 5 - Jun 6
8.2/10 Very Good! (1,017 reviews)
"Pool area’s were nice , the beach was nice could have raked it more often to keep dead grass washing up cleaned up"

Reviewed on Jun. 1, 2024

RumFish Beach Resort by TradeWinds
Sirata Beach Resort
Sirata Beach Resort
3 out of 5
5300 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jun. 26 to Jun. 27
CA $212
CA $301 total
includes taxes & fees
Jun 26 - Jun 27
7.2/10 Good! (2,250 reviews)
Great family resort!
"Great resort for families! We had a blast going from the beach to pool and to the splash pad. This resort had it all. Decent food and drink at their restaurants, and the daily live music was a nice touch too! We did encounter some minor hiccups, room keys kept deactivating, broken fan to name a couple, ..."

Reviewed on Jun. 1, 2024

Sirata Beach Resort
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Jul. 5 to Jul. 6
CA $189
CA $215 total
includes taxes & fees
Jul 5 - Jul 6
8.6/10 Excellent! (1,016 reviews)
"The staff is very nice and was very helpful when dealing with an issue I had and was quick to resolve it. If ever in Tampa again I will most definitely stay here again."

Reviewed on May 31, 2024

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
See all 15,559 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Family Vacations

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Frequently asked questions

How much does a Charter Oaks vacation package cost?
Custom make your Charter Oaks package from as little as CA $557. 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 vacation 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 vacation dreams.
Where should I stay in Charter Oaks?
A vacation 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 vacation?
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 vacation 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 traveling 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 organizing 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 vacation 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 organizing your Charter Oaks adventure.
If I'm not able to travel, can I cancel my Charter Oaks vacation package?
Don’t stress if you’re rethinking your Charter Oaks vacation 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.

Discover the most popular places to visit in Charter Oaks

Image for John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(136 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 check out its top-notch restaurants.

John's Pass Village & Boardwalk
Image for Tropicana Field

Tropicana Field

4/5(26 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.

Tropicana Field
Image for Fort De Soto Park

Fort De Soto Park

4.5/5(28 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

Things to do

Image for StarLite Majesty Evening Yacht Cruise Clearwater

StarLite Majesty Evening Yacht Cruise Clearwater

CA $43
Per adult
86% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Image for 2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $47
Per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Image for Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

CA $81
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
See all activities in St. Petersburg - Clearwater

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.