Chesterland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kristin DePlatchett

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 3.389.088 ₫ per night from 31 Aug to 1 Sept
3.389.088 ₫
3.982.177 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (1,513 reviews)
"Issue w shower water temp adjustment"

Reviewed on 18 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
Fully refundableReserve now, pay when you stay
The price is 4.048.968 ₫ per night from 24 Aug to 25 Aug
4.048.968 ₫
4.757.539 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Nice
"Beautiful place and lovely people."

Reviewed on 16 Aug 2025

Hyatt Regency Cleveland At The Arcade
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
2000 East Ninth Street, Cleveland, OH
Fully refundable
The price is 3.036.726 ₫ per night from 24 Aug to 25 Aug
3.036.726 ₫
3.568.152 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"This was a beautiful hotel that I also enjoyed thoroughly. It was extremely clean and I loved it."

Reviewed on 17 Aug 2025

Kimpton Schofield Hotel by IHG
See all 1,474 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.

Popular places to visit

Fowler's Mill Golf Course

Enjoy a round of golf in Chesterland at Fowler's Mill Golf Course. While in this quaint area, you can savour the top-notch restaurants.

Fowler's Mill Golf Course

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.