Cleveland Vacations

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Find the Best Cleveland Vacation Packages

Cleveland Hotel Deals

NEW! Shoreline Serenity
NEW! Shoreline Serenity
Cleveland
Shoreline Serenity is dreamy!
"This place is beautiful. It is decorated with a beachy theme that matches the breathtaking views. The attention to detail was superb and the little extras the owner added made our stay very special."

Reviewed on 1 April 2025

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NEW! Shoreline Serenity
Stunning castle with working vineyard - the ultimate luxury VRBO property!
Stunning castle with working vineyard - the ultimate luxury VRBO property!
Cleveland
9.8/10 Exceptional! (18 reviews)
Friends trip
"Property is awesome. Property was clean and in good condition. Property Manager was very good."

Reviewed on 21 February 2025

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Stunning castle with working vineyard - the ultimate luxury VRBO property!
Insane luxury beachfront estate - complete with indoor pool, arcade and theater!
Insane luxury beachfront estate - complete with indoor pool, arcade and theater!
Cleveland
9.8/10 Exceptional! (24 reviews)
Kohler Fall Challenge
"Our group of 12 have stayed over the weekend for the golf outing at the Whistling Straits Golf Course. Everyone loved this house and we had the best time ever. We will definitely come back in the near future. Thank you!!!"

Reviewed on 3 November 2024

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Insane luxury beachfront estate - complete with indoor pool, arcade and theater!
See all 540 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.

Frequently asked questions

How much does a Cleveland vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation to Cleveland costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Cleveland?
To score cheap Cleveland vacation packages, plan your trip outside of busy periods such as school holidays. You’ll generally find lower prices and better availability for flights and hotels.
How to find the best Cleveland package deals?
Use Expedia’s filter tool to find some unbeatable Cleveland package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your adventure for midweek, or search for Cleveland package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it’s usually best to book your vacation package as soon as possible.
Is it cheaper to book a Cleveland vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights individually. Better still, you can personalize your Cleveland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Cleveland?
If you’re considering an impromptu Cleveland adventure, check out our last-minute deals that can be booked up to one week before you go. Don’t want to leave things to the last minute? You can land incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Cleveland?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Cleveland.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your accommodations will probably be the largest expense during your trip to Cleveland.
  3. Work out your trip length: Think about how much time you’d like to spend discovering Cleveland. Plan your days so you can get to all the attractions and experiences you’re interested in at a leisurely pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to find a Cleveland vacation package that brings all your bookings together.