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.
Hampton Inn North Olmsted Cleveland Airport
Price was CA $1,139, price is now CA $1,013 per person
CA $1,013
per person
May 22 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9/10 Wonderful! (1,000 reviews)
Breakfast was fresh and room was nice and clean.
Reviewed on Apr 14, 2026
The Westin Cleveland Downtown
Downtown Cleveland
Price was CA $1,194, price is now CA $1,032 per person
CA $1,032
per person
May 22 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.6/10 Excellent! (2,104 reviews)
Only thing I wish was different I wish they would have included free breakfast with our stay , but other than that 10/10
Reviewed on Apr 13, 2026
Fidelity Hotel
Downtown Cleveland
Price was CA $1,484, price is now CA $1,287 per person
CA $1,287
per person
May 22 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9.6/10 Exceptional! (692 reviews)
We liked the room overall. The bed was very comfortable and the shower was great. We had an excellent breakfast in the Clubroom on our last morning. The location downtown was very convenient- close to attractions and restaurants.
We were at the hotel for two nights and the reservation included daily room service. That didn’t happen. We were out of the room all day and never received fresh towels or trash pickup. We also weren’t happy with the lighting in the vanity area. It was extremely dim and almost impossible to use the mirror above the sink.
Reviewed on Apr 12, 2026
Crowne Plaza Cleveland at Playhouse Square by IHG
Downtown Cleveland
Price was CA $1,283, price is now CA $1,132 per person
CA $1,132
per person
May 22 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (1,297 reviews)
Great location for the Cleveland International Film Festival. Always upholds their high standards for service.
Reviewed on Apr 15, 2026
Chesterland Hotel Deals
The Westin Cleveland Downtown
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Apr 23 to Apr 24
CA $205
CA $241 total
Apr 23 - Apr 24
includes taxes & fees
8.6/10 Excellent! (2,140 reviews)
Clean and updated room Awesome location Friendly Staff Rooms have a Beautiful lake view
Reviewed on Apr 14, 2026
Hotel Cleveland, Autograph Collection
24 Public Sq Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from May 3 to May 4
CA $184
CA $217 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (315 reviews)
Nice place
Reviewed on Apr 14, 2026
Holiday Inn Cleveland Clinic by IHG
8650 Euclid Ave Cleveland OH
Fully refundable
The price is CA $205 per night from May 1 to May 2
CA $205
CA $241 total
May 1 - May 2
includes taxes & fees
9/10 Wonderful! (1,320 reviews)
Staff was excellent. They had weird cleaning smell in the hotel. Good for a simple stay. The shower tub needs deep cleaning.
Reviewed on Apr 13, 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.
