Chesterland Vacations from $140
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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.
The Willoughby House
Save 100% on your flight
Price was $867, price is now $559 per person
$559
per person
Oct 27 - Nov 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
10/10 Exceptional! (2 reviews)
Beautiful property. Nice location. Excellent lounge & restaurant.
Reviewed on Aug 4, 2025
InterContinental Suites Hotel Cleveland by IHG
Fairfax
Save 100% on your flight
Price was $815, price is now $547 per person
$547
per person
Oct 27 - Nov 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,005 reviews)
Great property, very clean, safe. Front desk was nice, Valet was great/ $25 a night, The suite was amazing; 2 double beds in one room, living room/kitchen in the other room, tub and toilet in a separate from sink which makes it easy for everyone to get ready. We went to a concert at the Huntington Bank Field and booked here because the bus is pretty much a straight path there. However, be careful because the bus ride is much longer than we thought, it makes about 15 stops and we waited a while for it to even come. It’s only $5 for the day but we did Uber at one point because we didn’t want to be late. If you aren’t on a time crunch then this hotel is great for fairly close proximity to downtown.
Reviewed on Aug 24, 2025
Kimpton Schofield Hotel by IHG
Downtown Cleveland
Save 100% on your flight
Price was $664, price is now $448 per person
$448
per person
Oct 27 - Nov 1
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.6/10 Excellent! (1,002 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
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See all available trips from Columbus to Chesterland
View all tripsDiscover 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.
Chesterland Hotel Deals
The Westin Cleveland Downtown
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
Hyatt Regency Cleveland At The Arcade
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
Kimpton Schofield Hotel by IHG
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.