
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


The Willoughby House
Reviewed on Aug 4, 2025

InterContinental Suites Hotel Cleveland by IHG
Reviewed on Aug 24, 2025

Kimpton Schofield Hotel by IHG
Reviewed on Aug 23, 2025

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.
Chesterland Hotel Deals

The Westin Cleveland Downtown
Reviewed on Aug 25, 2025

Hyatt Regency Cleveland At The Arcade
Reviewed on Aug 22, 2025

Kimpton Schofield Hotel by IHG
Reviewed on Aug 23, 2025