Chesterland Vacations from $587

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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.
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Price was $770, price is now $587 per person
$587
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Cleveland (CLE)
7.4/10 Good! (1,004 reviews)
Very helpful staff! We enjoyed the poo

Reviewed on Feb 17, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $1,114, price is now $827 per person
$827
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Cleveland (CLE)
9/10 Wonderful! (843 reviews)
Some areas in the room were dusty. Customer service was excellent.

Reviewed on Feb 27, 2026

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was $818, price is now $611 per person
$611
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Cleveland (CLE)
8.4/10 Very Good! (1,442 reviews)
Amazing staff and room

Reviewed on Feb 26, 2026

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was $1,186, price is now $899 per person
$899
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Cleveland (CLE)
8.6/10 Excellent! (1,771 reviews)
Staff was pleasant and room was clean.

Reviewed on Feb 26, 2026

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $891, price is now $688 per person
$688
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Cleveland (CLE)
8.6/10 Excellent! (1,006 reviews)
The service was wonderful. Everyone that I encountered from the front desk to Betts were very helpful and welcoming. The room was very clean and the building was generally quiet.

Reviewed on Feb 27, 2026

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Discover the most popular places to visit in Chesterland

Fowler's Mill Golf Course

4/5(1 review)

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

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
$95 nightly
The price is $112 total per night from Mar 29 to Mar 30
$112 total
Mar 29 - Mar 30
Total with taxes and fees
8.4/10 Very Good! (1,585 reviews)
The room was clean and the staff was friendly. My only complaints were that there were no sheets or blankets in the room for the sofa bed, and the toilet paper was more like tissue paper. Other than those two things, the room was beautiful. I loved the shower and the shampoo, conditioner, body wash, ...

Reviewed on Feb 28, 2026

Hotel Indigo Cleveland Downtown by IHG
Hotel Cleveland, Autograph Collection

Hotel Cleveland, Autograph Collection

4 out of 5
24 Public Sq Cleveland OH
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $127 total per night from Mar 15 to Mar 16
$127 total
Mar 15 - Mar 16
Total with taxes and fees
9/10 Wonderful! (255 reviews)
Every single person I dealt with that worked for the hotel was a delight! They seem to really enjoy their job and they made me feel very comfortable. Strongly recommend this hotel definitely will stay again.

Reviewed on Feb 25, 2026

Hotel Cleveland, Autograph Collection
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
$140 nightly
The price is $165 total per night from Mar 1 to Mar 2
$165 total
Mar 1 - Mar 2
Total with taxes and fees
9/10 Wonderful! (1,123 reviews)
Great customer service, clean rooms and the pizza restaurant in the hotel as excellent!

Reviewed on Feb 26, 2026

Hyatt Regency Cleveland At The Arcade
See all 1,548 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 $587 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.