Chesterland Vacation Packages
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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.
Top Chesterland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kimpton Schofield Hotel by IHG
Downtown Cleveland
Price was CA $1,191, price is now CA $955 per person
CA $955
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.6/10 Excellent! (1,018 reviews)
Overall, our staff experience was quite satisfactory, and the hotel itself was generally pleasant. However, we encountered an issue with the room we booked, which featured a handicap-accessible bathroom. Unfortunately, whenever we would use the facilities, the entire bathroom became soaked, making it quite uncomfortable. When we reached out to the front desk to request a room change and also sought assistance from room service to help clean up the water, we were disappointed to find that no help was provided. This lack of response truly affected our stay.
Reviewed on Sep. 3, 2025
The Willoughby House
Price was CA $1,225, price is now CA $963 per person
CA $963
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
10/10 Exceptional! (4 reviews)
Clean rooms and comfortable beds helped us throughly enjoy our stay!
Reviewed on Aug. 26, 2025
The Westin Cleveland Downtown
Downtown Cleveland
Price was CA $1,539, price is now CA $1,232 per person
CA $1,232
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
8.6/10 Excellent! (1,549 reviews)
Staff was very friendly and the view was awesome
Reviewed on Sep. 3, 2025
Chesterland Hotel Deals
Ramada by Wyndham Cleveland Independence
5300 Rockside Road, Independence, OH
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Oct 1 to Oct 2
CA $99
CA $117 total
Oct 1 - Oct 2
includes taxes & fees
The Westin Cleveland Downtown
777 Saint Clair Ave Ne, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Sep 28 to Sep 29
CA $178
CA $209 total
Sep 28 - Sep 29
includes taxes & fees
Hyatt Regency Cleveland At The Arcade
420 Superior Ave E, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Sep 29 to Sep 30
CA $199
CA $233 total
Sep 29 - Sep 30
includes taxes & fees
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.