Cleveland Vacations from $462

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Photo by David Gayness

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.
Landing Apartments near North Fort Myers

Landing Apartments near North Fort Myers

4 out of 5
Hancock
Price was $614, price is now $462 per person
$462
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.4/10 Exceptional! (40 reviews)
The apartment was perfect, has everything that’s needed, I will never book a traditional hotel again. 10/10

Reviewed on Sep 2, 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,058, price is now $582 per person
$582
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,481 reviews)
Room very clean, the resort offers a wide range of dining, shopping, entertainment and well maintained pools

Reviewed on Sep 28, 2025

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was $792, price is now $529 per person
$529
per person
Nov 5 - Nov 9
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.8/10 Exceptional! (985 reviews)
Clean room great staff

Reviewed on Sep 27, 2025

Tranquility - Serene Waterfront Heated Pool Hot Tub

Tranquility - Serene Waterfront Heated Pool Hot Tub

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,291, price is now $1,067 per person
$1,067
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
No reviews
Hibiscus Heated Pool Private Dock Bikes Kayaks Walk to Fishermen s Village

Hibiscus Heated Pool Private Dock Bikes Kayaks Walk to Fishermen s Village

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,293, price is now $1,074 per person
$1,074
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
Boston (BOS) 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

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

Gilchrist Park

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

Charlotte County Historical Center

You can spend an afternoon exploring the galleries in Charlotte County Historical Center in Charlotte Harbor. Stroll along the waterfront or discover the beautiful sunsets in this quaint area.

Charlotte County Historical Center

What to do in Cleveland

"The Oasis" Tiki Boat

Sunset Tiki Boat Cruise (BYOB)

$59
per adult
Sunset Tiki Boat Cruise (BYOB)
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
Cape Coral and Fort Myers: Jet Ski Rental

Cape Coral and Fort Myers: Jet Ski Rental

$120
per traveler
Cape Coral and Fort Myers: Jet Ski Rental
See all activities in Cleveland

Cleveland Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $196 total per night from Oct 15 to Oct 16
$196 total
Oct 15 - Oct 16
Total with taxes and fees
9.2/10 Wonderful! (1,509 reviews)
"The resort is beautiful and the staff are wonderful…super accommodating, happy and very friendly!"

Reviewed on Sep 24, 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

2.5 out of 5
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
$67 nightly
The price is $75 total per night from Sep 30 to Oct 1
$75 total
Sep 30 - Oct 1
Total with taxes and fees
7.6/10 Good! (1,052 reviews)
"Newly renovated and great value"

Reviewed on Sep 21, 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
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
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $188 total per night from Sep 29 to Sep 30
$188 total
Sep 29 - Sep 30
Total with taxes and fees
9.6/10 Exceptional! (987 reviews)
"The suites are 2 bedroom. Around the boutiques, and shopping. Pool is nice. Just what we needed for a long weekend."

Reviewed on Sep 22, 2025

The Suites at Fishermen’s Village- 2 Bedroom Suites
See all 4,199 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.

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Frequently asked questions

How much does a Cleveland vacation package cost?
Offering great value package deals from $462 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.