Clearwater Beach Vacation Packages

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

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Top Holiday Package Deals in Clearwater Beach

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,257, price is now CA $797 per person
CA $797
per person
Aug 18 - Aug 22
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,114 reviews)
Great location and amenities were all as expected for a budget. Staff was friendly and helpful. We had a small issue but it was resolved quickly. No complaints and would recommend to others!

Reviewed on Jun 14, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,578, price is now CA $1,895 per person
CA $1,895
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Price was CA $2,447, price is now CA $1,499 per person
CA $1,499
per person
Jul 17 - Jul 19
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (929 reviews)
The location was still good for a Saturday stay with a lower rate b/c subway stations are close by as is Pier 11 to get over to DUMBO quickly. The neighborhood wasn’t a ghost-town even a good bit after midnight. Room was clean and nice.

Reviewed on Jun 7, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $1,800, price is now CA $1,115 per person
CA $1,115
per person
Jul 15 - Jul 18
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,055 reviews)
Clean room, good breakfast, and 1 block away from time square. It was a really good experience, and I would definitely stay here again.

Reviewed on Jun 14, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $4,448, price is now CA $2,774 per person
CA $2,774
per person
Jul 23 - Jul 26
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 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 $1,374 per night from Jun 18 to Jun 19
CA $1,374
CA $1,884 total
Jun 18 - Jun 19
includes taxes & fees
8.2/10 Very Good! (795 reviews)
"For a property charging roughly $1,500 per night, this was one of the most disappointing hotel experiences I’ve had. The issue started when I found bugs in my room. I called the front desk to ask if they had any mosquito or bug spray available and was told they did not. When I explained that there ..."

Reviewed on Jun 15, 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is CA $871 per night from Jun 28 to Jun 29
CA $871
CA $1,155 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (137 reviews)
"Clean room but they don’t come in to clean the room during your stay. Very good air conditioning. Spa only has one working shower"

Reviewed on Jun 14, 2026

Offshore Montauk
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is CA $510 per night from Jun 29 to Jun 30
CA $510
CA $610 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,357 reviews)
"all beautiful"

Reviewed on Jun 2, 2026

Montauk Manor
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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 $797. 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.