Chesterland Holidays

Photo by Kristin DePlatchett

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Top hotels in Chesterland

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
The price is €131 per night from 21 Aug to 22 Aug
€131
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (1,480 reviews)
Happy Momma
"Friendly staff, welcoming , clean . Recommend to stay . Walking distance to casino ."

Reviewed on 1 Aug 2025

The Westin Cleveland Downtown
Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
420 Superior Ave E, Cleveland, OH
The price is €132 per night from 24 Aug to 25 Aug
€132
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Lots of shopping and food choices within walking distance. Easy and safe walk to Progressive Field."

Reviewed on 2 Aug 2025

Hyatt Regency Cleveland At The Arcade
Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
651 Huron Rd E, Cleveland, OH
The price is €114 per night from 24 Aug to 25 Aug
€114
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (1,253 reviews)
"Everything was great"

Reviewed on 2 Aug 2025

Hotel Indigo Cleveland Downtown by IHG
See all 1,426 properties in Chesterland
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 Chesterland holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Chesterland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterland?
You can usually find reduced prices and better availability in January, February and November. Check out our cheap Chesterland holiday packages and you could score some great off-season deals.
How many days is enough for Chesterland?
The ideal duration for your Chesterland holiday depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to tick off all the leading sights and explore some hidden spots along the way.
How to find the best Chesterland package deals?
Begin your search for a Chesterland package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chesterland package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chesterland escape underway.
Is it cheaper to book a Chesterland holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Chesterland holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Chesterland?
If you're considering an impromptu Chesterland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterland?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the available activities will also help you decide when to visit Chesterland.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your hotel will probably be the largest expense during your trip to Chesterland.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to get to in Chesterland. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the perfect Chesterland holiday package for you.

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