Trilby Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Trilby Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
Price was $539, price is now $417 per person
$417
per person
Aug 27 - Sep 1
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Oldsmar. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oldsmar Flea Market and Tampa Bay Downs are located nearby.
Clearwater Beach Sheraton Resort on Sand Key
Sand Key
Save 100% on your flight
Price was $885, price is now $636 per person
$636
per person
Aug 27 - Sep 1
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach resort in Clearwater Beach. Enjoy 2 restaurants, a beach locale, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Our stay was amazing. There's a trolley that takes you to places that are family and tourist friendly. Beach is in walking distance. Our little ones had so much fun, the staff was amazing. We will be coming back for sure. Already making plans.
Reviewed on Jul 13, 2026
Pier House 60 Clearwater Beach Marina Hotel
Price was $674, price is now $491 per person
$491
per person
Aug 27 - Sep 1
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Wonderful location and staff. Bad breakfast tho
Reviewed on Jul 12, 2026
ChartHouse Clearwater Beach Marina Hotel
Save 100% on your flight
Price was $892, price is now $651 per person
$651
per person
Aug 27 - Sep 1
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Clean room, staff was so helpful, balcony had an amazing view, the pool was clean and so relaxing! We will definitely stay here again
Reviewed on Jul 12, 2026
The Westin Tampa Bay
Rocky Point
Price was $751, price is now $560 per person
$560
per person
Aug 27 - Sep 1
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach hotel in Tampa. Enjoy free WiFi, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Raymond James Stadium and George M. Steinbrenner Field are located nearby.
luxury at affordable place
Reviewed on Jul 12, 2026
Fairfield Inn & Suites by Marriott Clearwater Beach
Price was $731, price is now $546 per person
$546
per person
Aug 13 - Aug 18
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Clearwater Beach. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Very good
Reviewed on Jul 13, 2026
Top Hotel Deals
Saddlebrook Resort
5700 Saddlebrook Way Wesley Chapel FL
28.24 km from city center
Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our ...
SPOT X Hotel Tampa - Wesley Chapel by The Red Collection
5703 Oakley Blvd Wesley Chapel FL
29.46 km from city center
Book a stay at this business-friendly hotel in Wesley Chapel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn Zephyrhills - Dade City
6815 Gall Blvd Zephyrhills FL
22.88 km from city center
Book a stay at this business-friendly hotel in Zephyrhills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Wesley Chapel
5639 Oakley Blvd. Wesley Chapel FL
29.59 km from city center
Book a stay at this business-friendly hotel in Wesley Chapel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Days Inn by Wyndham Brooksville/Dade City
6320 Windmere Rd Brooksville FL
7.94 km from city center
Book a stay at this golf motel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Roadstar Hotel Zephyrhills
5734 Gall Blvd Zephyrhills FL
24.6 km from city center
Book a stay at this business-friendly motel in Zephyrhills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
Hampton Inn Dade City - Zephyrhills
13215 Us Highway 301 Dade City FL
12.49 km from city center
Stay at this hotel in Dade City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions The ...
Microtel Inn & Suites by Wyndham Zephyrhills
7839 Gall Blvd Zephyrhills FL
21.21 km from city center
Book a stay at this business-friendly hotel in Zephyrhills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express Hotel & Suites Brooksville West by IHG
14112 Cortez Blvd Spring Hill FL
30.52 km from city center
Book a stay at this business-friendly hotel in Spring Hill. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
Microtel Inn & Suites by Wyndham Bushnell
2612 West County Road 48 Bushnell FL
23.38 km from city center
Book a stay at this business-friendly hotel in Bushnell. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Microtel Inn & Suites by Wyndham Brooksville
6298 Nature Coast Blvd Brooksville FL
7.73 km from city center
Book a stay at this business-friendly hotel in Brooksville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Rodeway Inn Wesley Chapel
5642 Oakley Blvd Wesley Chapel FL
29.3 km from city center
Book a stay at this business-friendly hotel in Wesley Chapel. Enjoy free breakfast, free WiFi, and free parking. Popular attractions KRATE Shopping Center and ...
Fairfield Inn & Suites by Marriott Brooksville Suncoast Parkway
14082 Cortez Blvd Spring Hill FL
30.53 km from city center
Book a stay at this business-friendly hotel in Spring Hill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Aug 29 - Mon, Aug 31
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Tue, Aug 25 - Tue, Sep 1
LGA
LaGuardia
TPA
Tampa Intl.
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Tue, Aug 25 - Tue, Sep 1
LGA
LaGuardia
TPA
Tampa Intl.
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Tue, Sep 1 - Wed, Sep 16
ORD
O'Hare Intl.
TPA
Tampa Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Tue, Aug 25 - Wed, Aug 26
LGA
LaGuardia
TPA
Tampa Intl.
$162 Roundtrip, found 4 days ago
$162
Roundtrip
found 4 days ago