Cleveland Vacations from $576

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Your Cleveland Vacation

Book a Cleveland vacation package and prepare to experience all this city has to offer. Think about staying in the neighborhood of Punta Gorda Isles, which is great for walking, fishing and watersports. Fill your spare time with tours of Fishermens Village, Gilchrist Park and Bayshore Park Fishing Pier, some of the things you shouldn't miss during a trip to Cleveland. Whoever you're heading away with and whatever your bank balance, your ultimate Cleveland vacation is only clicks away with Expedia.

The Latest Cleveland vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $788, price is now $576 per person
$576
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (2,065 reviews)
The service at all the restaurants was terrible...

Reviewed on Mar 17, 2026

Nst108 4 Bedroom Home

Nst108 4 Bedroom Home

3 out of 5
Price was $1,568, price is now $1,450 per person
$1,450
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Punta Gorda Airport (PGD)
No reviews
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Discover the most popular places to visit in Cleveland

Peace River not far from Fisherman’s Village, Punta Gorda, Florida.

Fishermen's Village

4.5/5(322 reviews)

You can do some window-shopping at Fishermen's Village during your stay in Punta Gorda. Stroll along the waterfront in this family-friendly area, or check out its lively bars.

Fishermen's Village
Dramatic red sunset viewed from Bayshore Waterfront Park, New Jersey featuring fishing pier on the background

Bayshore Park Fishing Pier

3.5/5(2 reviews)

After visiting Bayshore Park Fishing Pier, make a plan to see the other sights and activities in Charlotte Harbor. Wander the waterfront or discover the beautiful sunsets in this quaint area.

Bayshore Park Fishing Pier
Statue of Juan Ponce de Leon (1460?-1521), who was a Spanish explorer and soldier who was the first European to set foot in Florida. He also established the oldest European settlement in Puerto Rico and discovered the Gulf Stream

Gilchrist Park

4/5(1 review)

Gilchrist Park is just one of the places to see in Punta Gorda, so why not enjoy the other things to explore during your travels? Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

Gilchrist Park

What to do in Cleveland

Night Sky Stargazing Tour in Punta Gorda Florida

Night Sky Stargazing Tour in Punta Gorda Florida

$59
per adult
Night Sky Stargazing Tour in Punta Gorda Florida
Marco Island: 10,000 Islands Shelling Boat Tour

Marco Island: 10,000 Islands Shelling Boat Tour

$100
per adult
100% of travellers recommend
Marco Island: 10,000 Islands Shelling Boat Tour
Wild dolphins on Charlotte Harbor!

Charlotte Harbor: Dolphin Discovery Day Cruise

$59
per adult
Charlotte Harbor: Dolphin Discovery Day Cruise
See all activities in Cleveland

Cleveland Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $267 total per night from Apr 6 to Apr 7
$267 total
Apr 6 - Apr 7
Total with taxes and fees
9.2/10 Wonderful! (2,131 reviews)
The service at all the restaurants was terrible...

Reviewed on Mar 17, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

3 out of 5
1941 Tamiami Trl Port Charlotte FL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from Apr 6 to Apr 7
$106 total
Apr 6 - Apr 7
Total with taxes and fees
7.6/10 Good! (1,007 reviews)
Good room

Reviewed on Mar 16, 2026

Days Inn by Wyndham Port Charlotte/Punta Gorda
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
$311 nightly
The price is $348 total per night from Apr 12 to Apr 13
$348 total
Apr 12 - Apr 13
Total with taxes and fees
9.8/10 Exceptional! (1,132 reviews)
Checking process was smooth and the staff was very friendly. The room was just outstanding (entertainment suite). Beautiful sunset view with a wrap around patio. The stairs outside the room go directly down to the brewhouse. We loved it and wished we could stay longer.

Reviewed on Mar 16, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
See all 4,538 properties in Cleveland
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.

Find the Best Cleveland Vacation Packages

Cleveland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlotte County Airport (PGD)
Top Sights
Peace River Wildlife Center & Ponce de León Park, Charlotte County Historical Center and Charlotte Harbor Preserve State Park

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Frequently asked questions

How much does a Cleveland vacation package cost?
Offering great value package deals from $576 on Expedia, you'll be pleasantly surprised at how much a vacation to Cleveland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cleveland?
June, August and October are the best times to look for cheap Cleveland vacation packages. Choosing to travel in less busy months means you'll typically find lower prices on accommodations and flights.
How many days is enough for Cleveland?
The ideal duration for your Cleveland vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to visit all the main sights and discover some hidden spots along the way.
How to find the best Cleveland package deals?
Begin your search for a Cleveland package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Cleveland package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cleveland escape off to a flying start.
Is it cheaper to book a Cleveland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Cleveland getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Cleveland?
If you've got your Cleveland vacation dates confirmed, book as soon as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Cleveland vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Cleveland trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.