Windsor Park Vacation Packages

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Top Holiday Package Deals in Windsor Park

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
6.6/10 (1,005 reviews)
Yes, its expensive but very quiet and clean. Quick train to all terminals

Reviewed on Mar. 4, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (374 reviews)
Great room and views. Very close to downtown Clearwater Beach. We did not have to use our car other than going to the Phillies games. The 5th floor bar area was a pleasant surprise also. Walk to the beach was great.

Reviewed on Mar. 3, 2025

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
May 12 - May 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
8.2/10 Very Good! (1,001 reviews)
Not enough dining & bar options when staying multiple days

Reviewed on Mar. 3, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
May 11 - May 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (313 reviews)
The room lovely and the staff were top notch!

Reviewed on Mar. 2, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
per person
May 28 - Jun. 2
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.2/10 Very Good! (37 reviews)
Very clean, texts from property management was clear, and professional. Thank you

Reviewed on Feb. 27, 2025

Where to stay in Windsor Park

Find the best Windsor Park areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Park
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

A noteworthy feature of Downtown St. Petersburg is its fantastic nightlife. While you're in town, be sure to stop and check out Tampa Bay and Jannus Live.

Find hotels in Downtown St. Petersburg

Windsor Park Hotel Deals

Wyndham Grand Clearwater Beach
Wyndham Grand Clearwater Beach
4 out of 5
100 Coronado Drive, Clearwater Beach, FL
The price is CA $411 per night from Apr. 1 to Apr. 2
CA $411
CA $515 total
includes taxes & fees
Apr 1 - Apr 2
9.2/10 Wonderful! (1,993 reviews)
Best hotel ever!
"We came here for the first time 3 years ago and have been coming back every year since It is the best hotel I’ve ever stayed at! The staff is amazing we got here before check in time and were able to check in That meant a lot to me We love the place"

Reviewed on Mar. 1, 2025

Wyndham Grand Clearwater Beach
RumFish Beach at TradeWinds
RumFish Beach at TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Mar. 5 to Mar. 6
CA $245
CA $367 total
includes taxes & fees
Mar 5 - Mar 6
8.2/10 Very Good! (1,214 reviews)
"Great hotel with great proximity to the beach and pools. Fun activities daily and very kind staff."

Reviewed on Mar. 2, 2025

RumFish Beach at TradeWinds
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 $405 per night from Mar. 10 to Mar. 11
CA $405
CA $515 total
includes taxes & fees
Mar 10 - Mar 11
7.8/10 Good! (1,741 reviews)
"The only problem I had was working my electronic door entry lock it failed 3 times and needed service it had to hold the handle and pull up on it and hold it completely up to push the door in"

Reviewed on Mar. 2, 2025

Hilton Clearwater Beach Resort & Spa
See all 13,976 properties in Windsor Park
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 Windsor Park vacation package cost?
Custom build your Windsor Park package from as little as CA $399. Choose from any combination of flights, hotels and rental cars to create the getaway you’ve long been dreaming about. Don’t forget to add on a few experiences or tours!
How do I get a cheap travel package to Windsor Park?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we’ve got it all. Choose the combination that suits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That’s why we offer over 550 airlines and 1,000,000 hotel options globally, which lets you customize your Windsor Park adventure.
Where should I stay in Windsor Park?
With fascinating attractions like Church of Scientology and Westfield Countryside Mall in this area, look for a hotel positioned near either one. Bright House Field is another sight that lures the crowds.
How far in advance should I book my Windsor Park vacation?
While prices change frequently, we generally recommend reserving your seat as soon as possible. Many international fares are found on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still be in luck. Cheaper tickets to Windsor Park sometimes appear in the weeks prior to departure.
What does an Expedia Windsor Park travel package include?
That depends on what sort of escape you want to have. Windsor Park vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that works for you! You can also add on activities and experiences after you’ve booked to get even bigger discounts.
What should I know before booking a Windsor Park travel package?
An Expedia travel package can be customized for your circumstances and is a terrific way to make your budget go further. How little or much you include is your call. Rental cars, hotels and flights — mix and match whatever combination works with your plans.
If I'm not able to travel, can I cancel my Windsor Park vacation package?
We totally get that life sometimes gets in the way of your plans. If you’ve locked in a Windsor Park vacation package and have to change or cancel it, we’re here to help. We recommend looking up our Customer Service Portal first for information. But generally speaking, if you’ve taken out your package in the last 24 hours, you may be able to cancel and rebook for free. If it’s more than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Windsor Park

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(136 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park
Vinoy Park

Vinoy Park

4.5/5(8 reviews)

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $45
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Bradenton: Adventure Course Entry Ticket

Bradenton: Adventure Course Entry Ticket

CA $103
per adult
Bradenton: Adventure Course Entry Ticket
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

CA $52
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.