Chesterland Vacations from $237

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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.
Bertram Inn at Glenmoor

Bertram Inn at Glenmoor

3.5 out of 5
Price was $298, price is now $237 per person
$237
per person
Feb 3 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Akron (CAK)
8.6/10 Excellent! (296 reviews)
Spacious room; very clean, staff was extremely welcoming. Easy check in and check out. Will definitely come back!

Reviewed on Dec 1, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $835, price is now $629 per person
$629
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Cleveland (CLE)
8.6/10 Excellent! (1,006 reviews)
Friendly staff nice hotel

Reviewed on Dec 12, 2025

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $758, price is now $579 per person
$579
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Cleveland (CLE)
9/10 Wonderful! (843 reviews)
Staying at the hotel was a great experience. The restaurants and room service were great. The staff was very helpful and pleasant.

Reviewed on Dec 8, 2025

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was $423, price is now $335 per person
$335
per person
Feb 3 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
8.8/10 Excellent! (1,231 reviews)
All in all terrific experience. Lots of patient family and friends relatives at the bar so misery loves company and a few glasses of wine and great IPA a welcome relief. Excellent shuttle to Cleveland Clinic.

Reviewed on Dec 10, 2025

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Price was $621, price is now $495 per person
$495
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Cleveland (CLE)
8.8/10 Excellent! (1,002 reviews)
Stayed there with some friends while visiting for an NFL game. The rooms were spacious and clean. Customer service was fantastic. The breakfast buffet was also enjoyable

Reviewed on Dec 8, 2025

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Discover the most popular places to visit in Chesterland

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 savor the top-notch restaurants.

Fowler's Mill Golf Course

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
$109 nightly
The price is $128 total per night from Dec 19 to Dec 20
$128 total
Dec 19 - Dec 20
Total with taxes and fees
8.6/10 Excellent! (1,895 reviews)
Nice room, good location, convenient parking garage, friendly staff

Reviewed on Dec 15, 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
$136 nightly
The price is $160 total per night from Jan 8 to Jan 9
$160 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8.8/10 Excellent! (1,077 reviews)
Great Hotel

Reviewed on Dec 16, 2025

Hyatt Regency Cleveland At The Arcade
Wyndham Independence

Wyndham Independence

4 out of 5
6200 Quarry Lane Independence OH
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $87 total per night from Dec 21 to Dec 22
$87 total
Dec 21 - Dec 22
Total with taxes and fees
6.4/10 (1,009 reviews)
Yes everything was great

Reviewed on Dec 14, 2025

Wyndham Independence
See all 1,533 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.

Find the Best Chesterland Vacation Packages

Chesterland Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Fowlers Mill Golf Course and Chardon Lakes Golf Club

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Frequently asked questions

How much does a Chesterland vacation package cost?
Offering great value package deals from $237 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.