Chesterland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hotel Indigo Cleveland Downtown by IHG
Downtown Cleveland
Price was CA $1,222, price is now CA $1,081 per person
CA $1,081
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cleveland (CLE)
8.4/10 Very Good! (1,686 reviews)
The room was clean and the bed was very comfortable. Elevator was slow, but there was an uprade in the process of beng completed. Close to Progressive Field and Rocket Arena. Rock and Roll Hall of Fame was about a 20 mins. walk. Most things were in reaosnable walking distance-restaurants, Downtown center, etc. Front receptionists were pleasant and informative. Would stay again.
Reviewed on Jun 3, 2026
InterContinental Suites Hotel Cleveland by IHG
Fairfax
Price was CA $1,510, price is now CA $1,323 per person
CA $1,323
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cleveland (CLE)
8.8/10 Excellent! (1,006 reviews)
While the room was clean and comfortable, the hallways were not. We were happy there was a bar/restaurant but the food and service were mediocre. To be fair, the serving staff was not adequate in number but the servers working were hustling and as attentive as possible. Kudos to the young woman at the front desk…extremely nice and helpful. Small but functional gym is available.
Reviewed on May 22, 2026
Holiday Inn Cleveland Clinic by IHG
Fairfax
Price was CA $1,431, price is now CA $1,254 per person
CA $1,254
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cleveland (CLE)
8.8/10 Excellent! (1,373 reviews)
Good location for Cleveland clinic and a descent restaurant on the 1st floor
Reviewed on May 31, 2026
ROOST Cleveland
Downtown Cleveland
Price was CA $2,807, price is now CA $2,469 per person
CA $2,469
per person
Aug 12 - Aug 16
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
9.6/10 Exceptional! (732 reviews)
Roost is a great value very large apartment style living in downtown. Couple small downsides, the bed is very low to the floor (but comfortable), HVAC is loud could be a problem for a light sleeper but I like background noise. Also because it is not a traditional hotel there is no restaurant or freshly made coffee in the morning so prepare for that accordingly.
Reviewed on Jun 1, 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 $249 per night from Jun 18 to Jun 19
CA $249
CA $292 total
Jun 18 - Jun 19
includes taxes & fees
8.8/10 Excellent! (2,194 reviews)
"Maintenance 24-7, even over a holiday weekend was obnoxious! Give your guests a break, at least at night."
Reviewed on Jun 2, 2026
Hotel Indigo Cleveland Downtown by IHG
651 Huron Rd E Cleveland OH
Fully refundable
The price is CA $163 per night from Jun 21 to Jun 22
CA $163
CA $191 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (1,699 reviews)
"The room was clean and the bed was very comfortable. Elevator was slow, but there was an uprade in the process of beng completed. Close to Progressive Field and Rocket Arena. Rock and Roll Hall of Fame was about a 20 mins. walk. Most things were in reaosnable walking distance-restaurants, Downtown ..."
Reviewed on Jun 3, 2026
Hilton Garden Inn Cleveland Downtown
1100 Carnegie Ave Cleveland OH
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Jun 21 to Jun 22
CA $165
CA $194 total
Jun 21 - Jun 22
includes taxes & fees
7.6/10 Good! (1,012 reviews)
"It was a clean hotel with a very friendly staff. We made use to the restaurant everyday. The food prices were very reasonable and we enjoyed the food and talking to the staff. We would definitely stay there again."
Reviewed on Jun 2, 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.
Stay near popular Chesterland attractions
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
