East Madison Vacation Packages for 2026
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East Madison Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Tampa North/I-75 Fletcher
New Tampa
Price was $702, price is now $518 per person
$518
per person
Jan 22 - Jan 28
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Tampa Bay and Seminole Hard Rock Casino Tampa are located nearby.
awesome
Reviewed on Nov 3, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was $1,398, price is now $867 per person
$867
per person
Jan 22 - Jan 28
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
The room and location were amazing! The pool being closed at sunset, along with the bathroom, was not optimal. We wanted to use the pool/hot tub in the evening after a day out and found it closed. Then we went to the bar and met people from another resort who left due to the bathroom being closed because the pool was closed(?). Jake(Bartender) and Katherine(Front desk) were awesome!!
Reviewed on Nov 3, 2026
Hyatt Regency Clearwater Beach Resort and Suites
Price was $1,601, price is now $1,129 per person
$1,129
per person
Jan 22 - Jan 28
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach resort in Clearwater Beach. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
The only complaint I have a the air conditioning only went down to 65 degrees and I felt super hot sleeping at night.
Reviewed on Nov 3, 2026
Holiday Inn Tampa Westshore - Airport Area by IHG
Westshore
Price was $890, price is now $641 per person
$641
per person
Jan 22 - Jan 28
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
Clearwater Beach Sheraton Resort on Sand Key
Sand Key
Price was $1,259, price is now $915 per person
$915
per person
Jan 22 - Jan 28
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Stay at this resort in Clearwater Beach. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sand Key Park and Pier 60 Park are located nearby.
Holiday Inn & Suites Clearwater Beach S-Harbourside by IHG
Price was $749, price is now $548 per person
$548
per person
Jan 22 - Jan 28
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this family-friendly hotel in Indian Rocks Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions St. Petersburg - Clearwater Beaches and Sand Key Park are located nearby.
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Fairfield Inn & Suites by Marriott Clearwater Beach
650 Bay Esplanade Clearwater Beach FL
30.62 km from East Madison
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 ...
HomeTowne Studios by Red Roof Tampa - Airport
6121 West Sitka Street Tampa FL
29.09 km from East Madison
Stay at this hotel in Tampa. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Raymond James Stadium and George M. Steinbrenner Field ...
Country Inn & Suites by Radisson, Tampa Airport North, FL
8109 Benjamin Road Tampa FL
29.25 km from East Madison
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
La Quinta Inn by Wyndham Clearwater Central
Clearwater FL
30.8 km from East Madison
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
Courtyard by Marriott Tampa Oldsmar
4014 Tampa Rd Oldsmar FL
23.68 km from East Madison
Book a stay at this business-friendly hotel in Oldsmar. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
3990 Tampa Rd Oldsmar FL
23.54 km from East Madison
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 ...
WoodSpring Suites Tampa Airport North Veterans Expressway
9310 Anderson Road Tampa FL
28.23 km from East Madison
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. ...
Innisbrook Resort
36750 Us Highway 19 N Palm Harbor FL
15.4 km from East Madison
Book a stay at this spa resort in Palm Harbor. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Best Western Plus Yacht Harbor Inn
150 Marina Plaza Dunedin FL
26.92 km from East Madison
Book a stay at this business-friendly hotel in Dunedin. Enjoy free breakfast, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
La Vista Inn
11736 US HIGHWAY 19 Port Richey FL
9.55 km from East Madison
Stay at this motel in Port Richey. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
13.61 km from East Madison
Book a stay at this business-friendly hotel in Tarpon Springs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful ...
Hotel Cabana Clearwater Beach
669 Mandalay Ave Clearwater Beach FL
30.56 km from East Madison
Book a stay at this beach motel in Clearwater Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in ...
Comfort Inn & Suites New Port Richey Downtown District
6206 US HWY 19 New Port Richey FL
2.06 km from East Madison
Book a stay at this business-friendly hotel in New Port Richey. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and ...
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.
Thu, Jan 14 - Thu, Jan 21
CLE
Hopkins Intl.
TPA
Tampa Intl.
$98 Roundtrip, found 17 hours ago
$98
Roundtrip
found 17 hours ago
Wed, Dec 2 - Tue, Dec 8
BOS
Logan Intl.
TPA
Tampa Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Tue, Dec 1 - Fri, Dec 4
MSP
Minneapolis - St. Paul Intl.
TPA
Tampa Intl.
$214 Roundtrip, found 4 hours ago
$214
Roundtrip
found 4 hours ago
Thu, Dec 3 - Sun, Dec 6
BOS
Logan Intl.
TPA
Tampa Intl.
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Wed, Jan 20 - Wed, Feb 3
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago