Chesterland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kristin DePlatchett

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Chesterland Holiday

Our pick of the best Chesterland Hotel Deals

The Westin Cleveland Downtown
The Westin Cleveland Downtown
4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is NZ$233 per night from 29 June to 30 June
NZ$233
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (1,396 reviews)
"Didn’t get the managers name but was such a great and helpful guy"

Reviewed on 22 Jun. 2025

The Westin Cleveland Downtown
Extended Stay America Premier Suites - Cleveland - Independence
Extended Stay America Premier Suites - Cleveland - Independence
2.5 out of 5
6025 Jefferson Dr, Independence, OH
Fully refundableReserve now, pay when you stay
The price is NZ$157 per night from 29 June to 30 June
NZ$157
29 June - 30 June
includes taxes & fees
7.4/10 Good! (1,616 reviews)
"$100 deposit required on top of the room fee This was not disclosed durung booking. The pool is permanently closed"

Reviewed on 22 Jun. 2025

Extended Stay America Premier Suites - Cleveland - Independence
Hyatt Regency Cleveland At The Arcade
Hyatt Regency Cleveland At The Arcade
4 out of 5
420 Superior Ave E, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is NZ$283 per night from 2 July to 3 July
NZ$283
2 July - 3 July
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Great building and people. Rppm smelled like smoke."

Reviewed on 22 Jun. 2025

Hyatt Regency Cleveland At The Arcade
See all 1,359 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.