Hillsborough County Vacation Packages

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Your Hillsborough County Vacation

Answer the call of adventure with a tailor-made vacation package to Hillsborough County. Wherever your travels take you and whatever you have planned, prepare to experience a destination that'll make you feel alive. With so much to see and do on a trip to Hillsborough County, it can be difficult to know where to begin. Kick off your travels in Tampa at Busch Gardens Tampa Bay and Raymond James Stadium — two popular attractions here. Another great city worth adding to your itinerary is Wesley Chapel. Don't miss Advent Health Centre Ice and Wesley Chapel District Park. Expedia has everything you need for planning your Hillsborough County vacation. From hotels and flights, to activities and more, we're here to help you create a travel experience like no other.

Top vacation destinations in Hillsborough County

FlightsFlightsHotelsHotels

Tampa

Tampa

Top Hillsborough County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,292, price is now CA $665 per person
CA $665
per person
Aug 7 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,004 reviews)
The room was clean staff was nice.i was good for the weekend stay really enjoyed it.

Reviewed on May 24, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $3,237, price is now CA $867 per person
CA $867
per person
Aug 11 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,149 reviews)
it was one night with my family friendly guy in the lobby very clean in the lobby and in the rooms clean bathroom and clean towels and also linen on the bed in the morning the breakfast was delicious and for different tastes there is also a children's room and a conference room and of course a swimming pool but we did not use it thanks to all the staff

Reviewed on Jun 1, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $3,028, price is now CA $1,264 per person
CA $1,264
per person
Aug 11 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.8/10 Excellent! (1,257 reviews)
Our stay was very pleasant, staff very polite! Great price!

Reviewed on Jun 1, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,953, price is now CA $954 per person
CA $954
per person
Aug 11 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (1,734 reviews)
Es super increíble me encantó

Reviewed on May 31, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $2,056, price is now CA $1,058 per person
CA $1,058
per person
Aug 11 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very Good! (6,490 reviews)
I loved everything about my trip, and when I checked in my room got upgraded! Best birthday trip for my kids & I it felt like home away from home! The property is set up to where I felt safe for 5 nights!

Reviewed on Jun 1, 2026

Hillsborough County Hotel Deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is CA $227 per night from Jun 28 to Jun 29
CA $227
CA $258 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,342 reviews)
"Very clean updated and modern room and decor. Staff was exceptionally friendly and helpful"

Reviewed on Jun 1, 2026

The Westin Tampa Bay
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $269 per night from Jun 7 to Jun 8
CA $269
CA $360 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (1,251 reviews)
"Beautiful property and rooms! The staff was very nice!"

Reviewed on May 31, 2026

Grand Hyatt Tampa Bay
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
111 W Fortune St Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jun 2 to Jun 3
CA $192
CA $220 total
Jun 2 - Jun 3
includes taxes & fees
8.6/10 Excellent! (2,619 reviews)
"We were in Tampa to visit family. The hotel was in a good location for our needs. They also gave a free shuttle that will take you within 2 miles. Staff was friendly. Rooms were clean but a little dated. Did not use the amenities we were only here to visit family."

Reviewed on Jun 1, 2026

The Barrymore Hotel Tampa Riverwalk
See all 4,440 properties in Hillsborough County
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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Frequently asked questions

How much does a Hillsborough County vacation package cost?
Chart your own course with our Hillsborough County vacation packages, which start from only CA $665. Select the hotels and flights that suit your travel style. Then, add on a few tours or experiences for an incredible escape.
How do I get a cheap travel package to Hillsborough County?
Browse and book everything in one place with our Hillsborough County vacation packages. You'll discover deals on hotels, flights and more that'll keep your credit card happy and your adventurousness alive. And, with more than 550 air carriers and 1,000,000 hotels around the globe to select from, you'll have endless opportunities to mix and match as you like.
Where should I stay in Hillsborough County?
Tampa is a great place to visit. It draws in many wanderers who come to explore its top sights, which include Raymond James Stadium and University of South Florida.
What are the top hotels in Hillsborough County?
For properties in Tampa with friendly service and cozy beds, you can't beat Hyatt Place Tampa Downtown and Seminole Hard Rock Hotel & Casino Tampa. If you're swinging by Plant City as well, you can look forward to a relaxing night's sleep at Ramada by Wyndham Tampa Westshore or Hampton Inn & Suites Tampa Airport Avion Park Westshore.
How far in advance should I book my Hillsborough County vacation?
Reserving your tickets early with Expedia means one less thing to have to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. Usually, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Hillsborough County sometimes become available just a few weeks before departure.
What does an Expedia Hillsborough County travel package include?
Expedia has everything you need to plan your Hillsborough County trip, but what goes into your package is your call. Pick from any combination of flights, hotels and rental cars. Looking for some activities or tours to keep you busy? Once you've made your booking, you can add them on too. Whatever your style, there's a vacation package to match your needs.
What should I know before booking a Hillsborough County travel package?
An Expedia travel package can be customized for your circumstances and is a great way to stretch your dollars further. How much you include is completely up to you. Rental cars, hotels and flights — decide on a combination that suits your style.
Can I choose my airline with a Hillsborough County Expedia vacation package?
Yes, and with over 550 airlines to choose from around the world, you've got lots of choice. Browse the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Hillsborough County vacation package?
Certainly, and we're here to help. You may be able to cancel or amend your Hillsborough County vacation package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company for older bookings. If life throws you a curveball, browse our Customer Service Portal for further information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.