Countryway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Outdoor pool
    Jul 25 - Jul 31

    ChartHouse Clearwater Beach Marina Hotel + Flight

    Clearwater Beach
    6 nights
    2.0 star property
    9.6/10 - Exceptional (1,029 reviews)
    "Nos encantó todo ! La habitación linda, limpia y amplia con una vista espectacular! Definitivamente volveremos lo recomiendo 10/10"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,662
    CA $1,072
    per traveller
    found 1 day ago
    ChartHouse Clearwater Beach Marina Hotel
  • Exterior
    Jun 29 - Jul 6

    The BC Resort on the Water + Flight

    St. Petersburg
    7 nights
    4.0 star property
    7.8/10 - Good (18 reviews)
    "We had a great stay at this condo during our trip to Florida. Everything was very clean and well maintained, which made it easy to relax right away. Communication was excellent—clear, prompt, and the instructions were simple to follow from check-in to check-out. The accommodations were comfortable and nicely set up, with everything we needed for our stay. The location was a big highlight—perfect for easy beach access and close to plenty of activities. We would definitely stay here again."
    Reviewed April 24, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,867
    CA $1,103
    per traveller
    found 1 day ago
    The BC Resort on the Water
  • 2 bedrooms, memory foam beds, in-room safe, blackout drapes
    Jun 29 - Jul 6

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    7 nights
    4.0 star property
    9.6/10 - Exceptional (968 reviews)
    "excellent"
    Reviewed May 17, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $3,177
    CA $1,882
    per traveller
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Exterior
    Jul 27 - Aug 3

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    7 nights
    3.0 star property
    9.2/10 - Wonderful (515 reviews)
    "Property was great! I would definitely recommend people to stay here great place parking is a bit of an issue if you have more than one car coming in but that comes with the island pretty typical but overall great "
    Reviewed May 17, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • Nonstop TPA - YYZ • Nonstop
    CA $2,532
    CA $1,588
    per traveller
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Outdoor pool, pool umbrellas, sun loungers
    Jun 29 - Jul 6

    Wyndham Grand Clearwater Beach + Flight

    Clearwater Beach
    7 nights
    4.0 star property
    9.4/10 - Exceptional (3,252 reviews)
    "Great breakfast, clean room, friendly staff!"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $3,228
    CA $2,071
    per traveller
    found 1 day ago
    Wyndham Grand Clearwater Beach

Where to stay in Countryway

Find the best Countryway areas and neighborhoods for the activities you enjoy most. Learn more about Countryway
Downtown Tampa

Downtown Tampa

5 out of top 10 points of interest in this area
4.5/5(56 area reviews)

Explore top attractions like the Florida Aquarium, Glazer Children's Museum, and Tampa Riverwalk, or indulge in the vibrant nightlife and dining scene in the River Arts District. Easily navigate the area with TECO Streetcar and HART public transportation.

Find hotels in Downtown Tampa

Countryway Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
The price is CA $369 per night from May 25 to May 26
CA $369
CA $471 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (3,252 reviews)
"Great breakfast, clean room, friendly staff!"

Reviewed on May 18, 2026

Wyndham Grand Clearwater Beach
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 $219 per night from May 25 to May 26
CA $219
CA $248 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,310 reviews)
"Sadly the pool was not open however Jimmy & Jenny at the bar were supre friendly and gave great service. The hotel staff was friendly"

Reviewed on May 18, 2026

The Westin Tampa Bay
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from May 25 to May 26
CA $232
CA $316 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,626 reviews)
"The amenities I read online were not free and even after showing the hotel they did nothing about it."

Reviewed on May 18, 2026

Hilton Clearwater Beach Resort & Spa
See all 12,776 properties in Countryway
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Countryway vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Countryway from just . And the more you bundle, the more dollars you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Countryway?
If you love amazing deals, bundle your bookings into a Countryway vacation package. Whether you're chasing flights, hotels, tours or rental cars, you can browse and book everything in one place. You'll have endless choice at your fingertips as well. Expedia has more than 550 airlines and 1,000,000 hotels around the globe to choose from. Fly with who you prefer, stay in a place you like and save a packet — now that's the perfect getaway!
Where should I stay in Countryway?
Most travelers who visit Countryway put both Port of Tampa and Raymond James Stadium on their must-see lists. Why not choose a hotel within walking distance of these great attractions?
How far in advance should I book my Countryway vacation?
While prices change from time to time, we generally suggest booking your seats as soon as possible. Many international airfares can be compared on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you may still get lucky. Discount prices to Countryway sometimes appear in the weeks prior to departure.
What does an Expedia Countryway travel package include?
It's up to you! You can pick from a variety of Countryway packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your perfect Countryway vacation looks like, you'll save!
What should I know before booking a Countryway travel package?
Whether it's adventure or relaxation you're seeking, a Countryway vacation package lets you plan your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Countryway Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have more than 550 partner airlines across the globe, so you have lots of choice when putting together your Countryway escape.
If I'm not able to travel, can I cancel my Countryway vacation package?
Whether it's your hotel or flight, you can cancel or change it. Locked in your Countryway vacation package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may be charged a fee by your airline, hotel or car rental company. For further information, visit our Customer Service Portal. We're here to help you every step of the way.

Discover the most popular places to visit in Countryway

Busch Gardens Tampa Bay

Busch Gardens Tampa Bay

4.5/5(79 reviews)

Exotic animals and thrill rides all on the one site at this theme park and zoo designed for the whole family.

Busch Gardens Tampa Bay
Tampa_RaymondJamesStadium_503050_03

Raymond James Stadium

4.5/5(30 reviews)

Catch an event at Raymond James Stadium during your trip to Tampa. Attend a football game or simply enjoy the top-notch restaurants while you're in the area.

Raymond James Stadium
Tampa Riverwalk

Tampa Riverwalk

4.5/5(93 reviews)

Walk, bike or rollerblade along Tampa’s waterside neighborhood, with public art, museums, restaurants and more attractions right on the waterfront.

Tampa Riverwalk

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $50
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $55
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
See all activities in Tampa
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.