Clearwater Beach Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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

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Top Holiday Package Deals in Clearwater Beach

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,165, price is now CA $1,362 per person
CA $1,362
per person
Apr 8 - Apr 12
found 23 hours ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Everything was ok. Nothing special

Reviewed on Feb 24, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $2,763, price is now CA $1,601 per person
CA $1,601
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (1,411 reviews)
I stayed here for 4 days with my girlfriend. The hotel is in a great spot with good food spots and cafes within walking distance. Staff are very attentive and helpful. The room is cozy and the shower is probably the best I've seen in a hotel or airbnb. Would 100% recommend

Reviewed on Feb 21, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,274, price is now CA $1,955 per person
CA $1,955
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
EVERYTHIING WAS 👌. 6 stars! Thank you Karla and the wonderful team.

Reviewed on Feb 21, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,607, price is now CA $2,217 per person
CA $2,217
per person
May 8 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Service at the hotel was fantastic!!! Beds are comfy, and bathrooms are very very nice!

Reviewed on Feb 21, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,248, price is now CA $1,407 per person
CA $1,407
per person
Apr 8 - Apr 12
found 23 hours ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,790 reviews)
Room was great. Buffet breakfast was amazing with so many options. Love the fact that a bar and coffee shop are downstairs next to the lobby.

Reviewed on Feb 24, 2026

Where to stay in Clearwater Beach

Find the best Clearwater Beach areas and neighborhoods for the activities you enjoy most. Learn more about Clearwater Beach
Wooden windmill with a wooden fence on a background of grass and blue sky

East Hampton North

Located on a picturesque peninsula, East Hampton boasts eight state parks and 70 miles of shoreline, perfect for nature lovers and beach enthusiasts. Explore charming hamlets like Montauk and Amagansett for a true Long Island experience.

Find hotels in East Hampton North

Clearwater Beach Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is CA $476 per night from Mar 26 to Mar 27
CA $476
CA $653 total
Mar 26 - Mar 27
includes taxes & fees
8.4/10 Very Good! (732 reviews)
The room was clean but was old and needed some updates and fixing. Staff were very friendly and courteous.

Reviewed on Feb 24, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is CA $158 per night from Feb 25 to Feb 26
CA $158
CA $207 total
Feb 25 - Feb 26
includes taxes & fees
9.2/10 Wonderful! (1,297 reviews)
Room was very nice

Reviewed on Feb 17, 2026

Montauk Manor
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $204 per night from Mar 26 to Mar 27
CA $204
CA $272 total
Mar 26 - Mar 27
includes taxes & fees
8.4/10 Very Good! (616 reviews)
The hotel was exceptional! We love staying at soundview during the winter months!

Reviewed on Feb 23, 2026

Sound View Greenport
See all 3,672 properties in Clearwater Beach
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.
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Frequently asked questions

How much does a Clearwater Beach vacation package cost?
Get ready to book, because a getaway to Clearwater Beach starts from an enticing CA $1,362. When you combine your flights, hotels and more into a package, you'll walk away with the best prices.
How do I get a cheap travel package to Clearwater Beach?
You'll save big if you combine your car rentals, hotels and flights into a Clearwater Beach vacation package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer more than 550 airlines and 1,000,000 properties all over the world, so you'll always have plenty of options to choose from. Like to save even more? Add some fun activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Clearwater Beach?
With lots to discover in Clearwater Beach, it'd be convenient for you to secure a room in a hotel near its attractions. Pollock-Krasner House and Study Center, Kaplan Meadows Sanctuary and Leiber Collection are some popular ones to add to your must-see list.
What are the top hotels in Clearwater Beach?
Secure a room at East Hampton Art House Bed And Breakfast. It's one of this area's most in-demand properties. Another top option in Clearwater Beach is Villa Hampton Hides.
How far in advance should I book my Clearwater Beach vacation?
Reward yourself with the biggest variety at the lowest prices by booking your adventure to Clearwater Beach nice and early. Air carriers tend to release tickets around 12 months prior to departure, so start locking things in as soon as you can. That being said, Expedia is constantly working to give you the best bargains around, so it's never a bad time to book your dream vacation!
What does an Expedia Clearwater Beach travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your dream Clearwater Beach getaway. You can also add on fun stuff like tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll get access to discounts you won't find elsewhere.
What should I know before booking a Clearwater Beach travel package?
A package can be easier on the wallet than separately booking everything you need for your adventure. For example, combine your hotels, flights and rental cars and save a tidy sum. Whatever sort of vacation you're planning, there's sure to be a package that fits your budget.
Can I choose my airline with a Clearwater Beach Expedia vacation package?
Yes, you sure can. We offer more than 550 airline partners worldwide, so choose the carrier that's a good fit for your budget needs.
If I'm not able to travel, can I cancel my Clearwater Beach vacation package?
Don't worry if you're rethinking your Clearwater Beach vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We know life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in Clearwater Beach

East Hampton Main Beach

East Hampton Main Beach

On the eastern edge of Long Island, enjoy a day on this exclusive beach complete with lifeguards, restrooms, a snack bar and other amenities.

East Hampton Main Beach
LongHouse Reserve which includes outdoor art, a park and wild flowers

LongHouse Reserve

Walk among many acres of lush gardens in East Hampton and discover a stunning array of sculptures and art installations.

LongHouse Reserve
Pollack-Krasner House and Studio which includes a house

Pollock-Krasner House and Study Center

In this unassuming studio in East Hampton, see where two of America’s foremost abstract painters created some of their most famous works.

Pollock-Krasner House and Study Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.