Chesterland Trips (flight + hotel)

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
Fully refundableReserve now, pay when you stay
The price is P7,365 per night from Aug 21 to Aug 22
P7,365
P8,654 total
Aug 21 - Aug 22
includes taxes & fees
8.4/10 Very Good! (1,495 reviews)
"comfortable room tho trouble getting cold water out of shower and sink"

Reviewed on Aug 8, 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
Fully refundableReserve now, pay when you stay
The price is P7,422 per night from Sep 1 to Sep 2
P7,422
P8,721 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Totally amazing building — a true architectural gem. We were a little astonished actually by the remarkable interior. Good, polite staff . . . everything fine. View from our window wasn’t great, but it’s okay. We weren’t in the room much anyway. Very cool that the staff wore Cleveland Guardians jerseys! ..."

Reviewed on Aug 9, 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
Fully refundable
The price is P6,395 per night from Aug 24 to Aug 25
P6,395
P7,514 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,267 reviews)
"Overall good. Property not around a lot of well-known food places: Starbucks, Panera Bread, etc. Location was basically dead. Property very nice, updated. Would recommend."

Reviewed on Aug 9, 2025

Hotel Indigo Cleveland Downtown by IHG
See all 1,468 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 vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation packages and you could score some great off-season deals.
How many days is enough for Chesterland?
The ideal duration for your Chesterland vacation 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 vacation as a package?
Expedia vacation 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 vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 accommodations: Once you've nailed down your trip dates and duration, lock in the perfect Chesterland vacation package for you.

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