Winston Park Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Winston Park

Find the best Winston Park areas and neighborhoods for the activities you enjoy most. Learn more about Winston Park
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area
5/5(3 area reviews)

Pass-a-Grille is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to Pass-a-Grille Beach or St. Petersburg - Clearwater Beaches.

Find hotels in Pass-a-Grille

Top hotels in Winston Park

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
The price is 8.882.469 ₫ per night from 25 May to 26 May
8.882.469 ₫
11.079.172 ₫ total
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (3,252 reviews)
"Great breakfast, clean room, friendly staff!"

Reviewed on 18 May 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 4.569.437 ₫ per night from 7 Jun to 8 Jun
4.569.437 ₫
5.186.074 ₫ total
7 Jun - 8 Jun
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 18 May 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 5.771.088 ₫ per night from 25 May to 26 May
5.771.088 ₫
7.563.550 ₫ total
25 May - 26 May
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 18 May 2026

Hilton Clearwater Beach Resort & Spa
See all 16,961 properties in Winston 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.

Frequently asked questions

How much does a Winston Park holiday package cost?
We make it easy to explore the world, with Winston Park packages starting from just . You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add some activities and tours to your travel itinerary?
How do I get a cheap travel package to Winston Park?
Book everything in the one place with our Winston Park holiday packages. You'll find bargains on flights, hotels, tours and more that'll keep your travel budget happy and your sense of adventure alive. And, with more than 550 air carriers and 1null000null000 properties around the globe to select from, you'll have the flexibility to mix and match as you want.
Where should I stay in Winston Park?
Urban explorers come from all corners of the globe to see Salvador Dali Museum and Tropicana Field in Winston Park. Book a room close to these terrific attractions and visit them whenever you want.
How far in advance should I book my Winston Park holiday?
It can be tricky to know when the best time is to book your Winston Park trip. But generally the earlier you book, the better the prices. In some cases, you can lock in your flights and hotels up to a year before your departure date. If you're thinking of a last-minute getaway, no need to panic! There are fabulous bargains popping up on Expedia every single day.
What does an Expedia Winston Park travel package include?
You can choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like experiences and activities. Want to pick your fare class? That's also easy to do. The choice is all yours when it comes to planning your ideal Winston Park getaway.
What should I know before booking a Winston Park travel package?
Our prices are already low. However, you'll pick up an even better deal when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Winston Park Expedia holiday package?
You can, and with over 550 airlines to select from globally, you've got lots of choice. Look through the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Winston Park holiday package?
Yes, it's possible to cancel your Winston Park booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Popular places to visit

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

4.5/5(34 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the marina in this family-friendly area or visit its lively bars.

John's Pass Village & Boardwalk
Fort De Soto Park

Fort De Soto Park

4.5/5(25 reviews)

Enjoy the beautiful sunsets and explore Fort De Soto Park, a lovely green space in Tierra Verde. Discover the top-notch restaurants and great live music in this family-friendly area.

Fort De Soto Park
Vinoy Park

Vinoy Park

After visiting Vinoy Park, make a plan to see the other sights and activities in St. Petersburg. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Vinoy Park