Clearwater Beach Vacation Packages

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  • Better together

    Save up to CA $4,200 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 New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,314, price is now CA $1,306 per person
CA $1,306
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,213 reviews)
We were SUPER impressed with the hotel cleanliness and the staff was very, very friendly and helpful. This hotel offers express checkout. There was no need today to line up and speak to anyone to check out. We just dropped our key in the designated box and left at checkout time. Super convenient. Breakfast was absolutely delicious with a large assortment of choices. To use the elevator it required a room key which was a nice security feature. The only complaint we had was the size of the actual room. Our room had a queen bed. There was room to walk around the bed but not much more. But for the price? This hotel was well worth the stay.

Reviewed on Jul 30, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,318, price is now CA $1,308 per person
CA $1,308
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)
Great property

Reviewed on Jul 30, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,941, price is now CA $2,825 per person
CA $2,825
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
This hotel is something out of the world beautiful

Reviewed on Jul 29, 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was CA $2,745, price is now CA $1,575 per person
CA $1,575
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (719 reviews)

The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Price was CA $9,983, price is now CA $6,063 per person
CA $6,063
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Very clean and friendly staff

Reviewed on Jul 28, 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
A traditional windmill with a wooden fence in the foreground.

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

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
8.4/10 Very good! (672 reviews)
"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went ..."

Reviewed on Jul 29, 2026

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Sound View Greenport
Montauk Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
The price is CA $1,052 per night from Aug 30 to Aug 31
CA $1,052
CA $1,362 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great service! Especially the wait staff"

Reviewed on Jul 28, 2026

Montauk Yacht Club
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $378 per night from Aug 16 to Aug 17
CA $378
CA $467 total
Aug 16 - Aug 17
includes taxes & fees
The Atlantic Hotel
See all 3,665 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 $1,306. 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.

Stay near popular Clearwater Beach attractions

Kaplan Meadows Sanctuary

Enjoy an outing to Kaplan Meadows Sanctuary during your stay in Springs. Wander the beautiful beaches and seaside in the area.
See properties

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

CA $248
per adult
Sunday Brunch Sail in Greenport
See all activities in East Hampton
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.