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.
Hilton Garden Inn Cleveland Downtown
Downtown Cleveland
Price was CA $1,636, price is now CA $1,385 per person
CA $1,385
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
7.4/10 Good! (1,004 reviews)
Very helpful staff! We enjoyed the poo
Reviewed on Feb 17, 2026
Hotel Indigo Cleveland Downtown by IHG
Downtown Cleveland
Price was CA $1,922, price is now CA $1,496 per person
CA $1,496
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
8.4/10 Very Good! (1,442 reviews)
Amazing staff and room
Reviewed on Feb 26, 2026
The Westin Cleveland Downtown
Downtown Cleveland
Price was CA $2,321, price is now CA $1,878 per person
CA $1,878
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
8.6/10 Excellent! (1,771 reviews)
Staff was pleasant and room was clean.
Reviewed on Feb 26, 2026
ROOST Cleveland
Downtown Cleveland
Price was CA $1,892, price is now CA $1,618 per person
CA $1,618
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
9.6/10 Exceptional! (597 reviews)
Absolutely loved this property. The location is perfect, and the entire space has been beautifully renovated with high-end materials and a sleek, modern feel. The two-bedroom layout with two full bathrooms made it incredibly spacious and comfortable.
The staff was super friendly and welcoming, which made the stay even better.
And the best part? Le Labo Santal 33 toiletries — my absolute favorite. Such a luxurious, thoughtful touch. I didn’t want to leave.
Reviewed on Feb 24, 2026
Chesterland Hotel Deals
Hotel Indigo Cleveland Downtown by IHG
651 Huron Rd E Cleveland OH
Fully refundable
The price is CA $139 per night from Mar 22 to Mar 23
CA $139
CA $163 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,584 reviews)
The room was clean but the breakfast food wasn't ready as if they were either short handed for two days and or didn't no the number of people in the hotel to prepare.
Reviewed on Feb 28, 2026
Hotel Cleveland, Autograph Collection
24 Public Sq Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Mar 15 to Mar 16
CA $147
CA $173 total
Mar 15 - Mar 16
includes taxes & 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
Hyatt Regency Cleveland At The Arcade
420 Superior Ave E Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Mar 1 to Mar 2
CA $191
CA $224 total
Mar 1 - Mar 2
includes taxes & 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
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.
