Chesterland Vacations from $140

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Photo by Kristin DePlatchett

Your Chesterland Vacation

Build a custom vacation package to Chesterland and start looking forward to your next big adventure. Stay in the neighborhood of Shaker Heights, which is great for cafes and golfing, for a real taste of this vibrant city. If going to see the sights is a priority during your trip to Chesterland, make sure you find your way to famous attractions like Alpine Valley and Fowlers Mill Golf Course. Expedia is here to help you escape the everyday. Tailor your vacation to Chesterland to suit your travel style, whatever that may look like.

The Latest Chesterland vacation packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Independence
The Willoughby House
InterContinental Suites Hotel Cleveland by IHG
Kimpton Schofield Hotel by IHG
Hampton Inn & Suites Cleveland/Independence
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Discover the most popular places to visit in Chesterland

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
$129 nightly
The price is $152 total per night from Sep 1 to Sep 2
$152 total
Sep 1 - Sep 2
Total with taxes and fees
8.4/10 Very Good! (1,539 reviews)
"Good location in downtown Cleveland with easy walkable access to many attractions. Self-parking could be a bit of a challenge and would be nice to have a shop where one could get beverages after hours. Still a good experience."

Reviewed on Aug 25, 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
$159 nightly
The price is $187 total per night from Sep 1 to Sep 2
$187 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
"Great hotel!"

Reviewed on Aug 22, 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 refundableReserve now, pay when you stay
$122 nightly
The price is $144 total per night from Sep 1 to Sep 2
$144 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"The staff at this hotel are amazing! The hotel itself is clean and modern and within walking distance from many attractions. The only “downside” we experienced was an odd loud whirring type noise outside our window at night."

Reviewed on Aug 23, 2025

Kimpton Schofield Hotel by IHG
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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Frequently asked questions

How much does a Chesterland vacation package cost?
Offering great value package deals from $140 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?
January, April and September are the best times to search for cheap Chesterland vacation packages. Choosing to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Chesterland?
The ideal duration for your Chesterland vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to tick off all the leading attractions and explore some hidden treasures 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.
Does Expedia offer Book Now, Pay Later Chesterland vacation packages?
Your Chesterland trip is meant to be an escape from your busy life, not a reason for money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.