Chesterland Holidays from AU$1,327

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Your Chesterland Holiday

Come and experience this captivating city for yourself with a Chesterland holiday package. Think about staying in the neighbourhood of Shaker Heights, which is good for cafes and golfing, and your time here is sure to be unforgettable. There's plenty to see during your trip to Chesterland, including Alpine Valley and Fowlers Mill Golf Course. Your Chesterland holiday is just clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

The Latest Chesterland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Bertram Inn at Glenmoor

Bertram Inn at Glenmoor

3.5 out of 5
per person
25 Sept - 1 Oct
found 1 day ago
Return direct flight included
Calgary (YYC) to Akron (CAK)
8.6/10 Excellent! (276 reviews)
Property is in a quiet spot and it feels peaceful on the property.

Reviewed on 27 Jul. 2025

Hampton Inn Medina

Hampton Inn Medina

2.5 out of 5
per person
25 Sept - 1 Oct
found 1 day ago
Return direct flight included
Calgary (YYC) to Akron (CAK)
8.8/10 Excellent! (949 reviews)
Was would visit again

Reviewed on 27 Jul. 2025

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

The Bertram Inn & Conf Ctr Trademark Collection by Wyndham

3.5 out of 5
per person
25 Sept - 1 Oct
found 1 day ago
Return direct flight included
Calgary (YYC) to Akron (CAK)
7.6/10 Good! (171 reviews)
Positives: Quiet and clean. Not sure at what price point actual bedding should be expected. This room was $180 plus tax. Two sheets and a light blanket were the “bedding”. The room was quiet both nights, I was surprised there was no coffee available in the mornings. My only negative is the lack of bedding.

Reviewed on 21 Jul. 2025

Kent State University Hotel and Conference Center

Kent State University Hotel and Conference Center

3.5 out of 5
per person
25 Sept - 1 Oct
found 1 day ago
Return direct flight included
Calgary (YYC) to Cleveland (CLE)
9.4/10 Exceptional! (1,021 reviews)
All around, the hotel was clean, modern and comfortable. The staff was friendly at the front desk and in the restaurant. We ate breakfast in the restaurant and it was delicious. The neighborhood was trendy with all types of businesses and plenty of restaurants from which to choose. A+

Reviewed on 30 Jul. 2025

Courtyard by Marriott Canton

Courtyard by Marriott Canton

3 out of 5
per person
25 Sept - 1 Oct
found 1 day ago
Return direct flight included
Calgary (YYC) to Akron (CAK)
8.4/10 Very Good! (910 reviews)
It was fine for what we needed

Reviewed on 24 Jul. 2025

Chesterland Holiday

Chesterland Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Lake Lucerne Beach, Chardon Lakes Golf Club and Fowlers Mill Golf Course

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
The price is AU$234 per night from 21 Aug to 22 Aug
AU$234
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (1,488 reviews)
Overall good
"Service was ok while checking in, some of the front desk employees seemed aloof and didn’t care if you were standing there waiting in line while someone cut in front of you etc. Also upon check out there was no help offered for the 100$ hold that is placed on your card at check in (which they don’t ..."

Reviewed on 3 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 AU$236 per night from 1 Sept to 2 Sept
AU$236
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Great stay!"

Reviewed on 4 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 AU$203 per night from 24 Aug to 25 Aug
AU$203
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.
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All Inclusive Holidays
All Inclusive Holidays
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Frequently asked questions

How much does a Chesterland holiday package cost?
Offering great value package deals from AU$1,327 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.