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 $927, price is now CA $827 per person
CA $827
per person
Apr 13 - Apr 16
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
7.4/10 Good! (1,004 reviews)
Very helpful staff! We enjoyed the poo
Reviewed on Feb 17, 2026
Embassy Suites by Hilton Cleveland Rockside
Price was CA $1,012, price is now CA $916 per person
CA $916
per person
Apr 13 - Apr 16
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
7.4/10 Good! (1,002 reviews)
super nice view of the city !clean room and kind front desk attendant
Reviewed on Feb 25, 2026
Crowne Plaza Cleveland Airport by IHG
Price was CA $1,871, price is now CA $1,707 per person
CA $1,707
per person
May 4 - May 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
7.2/10 Good! (1,001 reviews)
Loved the bed. Loved the ease of long term car parking, and the airport shuttle. Would have left a four star review, but coffee maker did not work, no coffee made in the lobby when I left at 4:30, and tub shower did not drain.
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 $131 per night from Mar 1 to Mar 2
CA $131
CA $154 total
Mar 1 - Mar 2
includes taxes & fees
8.4/10 Very Good! (1,580 reviews)
Amazing staff and room
Reviewed on Feb 26, 2026
Hotel Cleveland, Autograph Collection
24 Public Sq Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Feb 28 to Mar 1
CA $148
CA $174 total
Feb 28 - Mar 1
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 Feb 28 to Mar 1
CA $191
CA $225 total
Feb 28 - Mar 1
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.
