Cheap Vacations in Hillsborough County

Choose two or more items and save on your trip:

Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,411, price is now $446 per person
$446
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,176, price is now $590 per person
$590
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $1,113, price is now $569 per person
$569
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $1,112, price is now $591 per person
$591
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,405, price is now $772 per person
$772
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $2,312, price is now $1,288 per person
$1,288
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $855, price is now $494 per person
$494
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,602, price is now $1,013 per person
$1,013
per person
Jul 16 - Jul 20
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Save 100% on your flight
Price was $1,435, price is now $948 per person
$948
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $989, price is now $681 per person
$681
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

3-night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Vero Beach Inn & Suites I-95

Vero Beach Inn & Suites I-95

3 out of 5
Price was $481, price is now $345 per person
$345
per person
Jul 24 - Jul 27
found 12 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,222, price is now $459 per person
$459
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $1,830, price is now $1,144 per person
$1,144
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $723, price is now $471 per person
$471
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Price was $555, price is now $362 per person
$362
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,110, price is now $740 per person
$740
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $784, price is now $525 per person
$525
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $638, price is now $448 per person
$448
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $869, price is now $612 per person
$612
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Best Western Aku Tiki Inn

Best Western Aku Tiki Inn

2.5 out of 5
Price was $569, price is now $406 per person
$406
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,514, price is now $1,085 per person
$1,085
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Price was $677, price is now $489 per person
$489
per person
Jul 10 - Jul 13
found 11 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)

4-night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $556, price is now $374 per person
$374
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,112, price is now $591 per person
$591
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $2,071, price is now $1,268 per person
$1,268
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $861, price is now $531 per person
$531
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $762, price is now $480 per person
$480
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,602, price is now $1,013 per person
$1,013
per person
Jul 16 - Jul 20
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Orlando (MCO)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was $708, price is now $477 per person
$477
per person
Jul 13 - Jul 17
found 13 hours ago
Roundtrip flight included
New York (NYC) to Tampa (TPA)
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Save 100% on your flight
Price was $857, price is now $588 per person
$588
per person
Jul 16 - Jul 20
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $989, price is now $681 per person
$681
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $808, price is now $561 per person
$561
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,410, price is now $984 per person
$984
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $799, price is now $560 per person
$560
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

5-night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $700, price is now $443 per person
$443
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,411, price is now $446 per person
$446
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,483, price is now $713 per person
$713
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $2,518, price is now $1,392 per person
$1,392
per person
Jul 15 - Jul 20
found 3 hours ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $910, price is now $532 per person
$532
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $859, price is now $508 per person
$508
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,591, price is now $991 per person
$991
per person
Jul 5 - Jul 10
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $949, price is now $597 per person
$597
per person
Jul 22 - Jul 27
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $1,241, price is now $814 per person
$814
per person
Jul 12 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
San José (SJO) to Orlando (MCO)
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Save 100% on your flight
Price was $822, price is now $540 per person
$540
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $807, price is now $542 per person
$542
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Save 100% on your flight
Price was $850, price is now $570 per person
$570
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)

6-7 night Hillsborough County vacations

Price found within the past 48 hours. Click for updated prices.
Alhambra Villas

Alhambra Villas

3 out of 5
Save 100% on your flight
Price was $624, price is now $393 per person
$393
per person
Jul 7 - Jul 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,643, price is now $482 per person
$482
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,176, price is now $590 per person
$590
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $1,113, price is now $569 per person
$569
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CW Hotel

CW Hotel

2 out of 5
Save 100% on your flight
Price was $3,002, price is now $1,605 per person
$1,605
per person
Jul 16 - Jul 22
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,405, price is now $772 per person
$772
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $2,312, price is now $1,288 per person
$1,288
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $1,283, price is now $725 per person
$725
per person
Jul 14 - Jul 20
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $855, price is now $494 per person
$494
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,160, price is now $750 per person
$750
per person
Jul 20 - Jul 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Save 100% on your flight
Price was $1,139, price is now $737 per person
$737
per person
Jul 19 - Jul 26
found 15 hours ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $1,025, price is now $667 per person
$667
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)

Top places to visit in Hillsborough County

FlightsFlightsHotelsHotels

Tampa

Tampa

Flight deals to Hillsborough County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 5 - Sat, Aug 8
TTN
Trenton
TPA
Tampa
$82 Roundtrip, found 7 hours ago
$82
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Trenton to Tampa, returning Sat, Aug 8, priced at $82 found 7 hours ago
Sat, Jul 25 - Wed, Jul 29
PHL
Philadelphia
TPA
Tampa
$92 Roundtrip, found 6 days ago
$92
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jul 25 from Philadelphia to Tampa, returning Wed, Jul 29, priced at $92 found 6 days ago
Mon, Jul 13 - Thu, Jul 16
CLE
Cleveland
TPA
Tampa
$121 Roundtrip, found 7 hours ago
$121
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Jul 13 from Cleveland to Tampa, returning Thu, Jul 16, priced at $121 found 7 hours ago

Top rated hotels for your Hillsborough County vacation

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Free Cancellation
6.69 mi from city center
The price is $163 total per night
$163 total
per night
Jun 28 - Jun 29
With a stay at The Westin Tampa Bay in Tampa (Rocky Point), you'll be a 1-minute drive from Tampa Bay and 8 minutes from Raymond James Stadium.
On private beach
Pet friendly
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
111 W Fortune St Tampa FL
Free Cancellation
Reserve now, pay when you stay
0.44 mi from city center
The price is $144 total per night
$144 total
per night
Jun 2 - Jun 3
With a stay at The Barrymore Hotel Tampa Riverwalk, you'll be centrally located in Tampa, within a 10-minute walk of Tampa Museum of Art and Tampa Theater.
Pool
Pet friendly
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
3001 University Center Dr Tampa FL
Free Cancellation
Reserve now, pay when you stay
6.96 mi from city center
The price is $158 total per night
$158 total
per night
Jun 1 - Jun 2
With a stay at OASIS BAY SUITES, Tampa, Busch Gardens, USF, you'll be centrally located in Tampa, within a 5-minute drive of University of South Florida and Busch Gardens Tampa Bay.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Hillsborough County
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.