
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.

Holiday Inn Cleveland Clinic by IHG
Fairfax
Price was CA $722, price is now CA $624 per person
CA $624
per person
Oct 18 - Oct 20
found 6 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Cleveland (CLE)
8.8/10 Excellent! (1,183 reviews)
Proximity to Cleveland Clinic and willingness to accomodate early check in and late check out for patients with appointments (within reason and when possible).
Reviewed on Aug. 25, 2025

InterContinental Suites Hotel Cleveland by IHG
Fairfax
Price was CA $817, price is now CA $689 per person
CA $689
per person
Oct 18 - Oct 20
found 6 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Cleveland (CLE)
8.8/10 Excellent! (1,004 reviews)
Great staff, nice room
Reviewed on Aug. 31, 2025

The Westin Cleveland Downtown
Downtown Cleveland
Price was CA $1,091, price is now CA $932 per person
CA $932
per person
Oct 18 - Oct 20
found 6 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Cleveland (CLE)
8.6/10 Excellent! (1,549 reviews)
Great views of downtown Cleveland to include the stadium and Lak Erie.
Reviewed on Aug. 31, 2025

Kimpton Schofield Hotel by IHG
Downtown Cleveland
Price was CA $1,119, price is now CA $960 per person
CA $960
per person
Oct 18 - Oct 20
found 6 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Cleveland (CLE)
8.6/10 Excellent! (1,018 reviews)
Not a fan of the non existent parking….as there was not any. If there is an event going on when you check in pay for the valet, definitely worth it rather than the hassle of finding parking. Something I wish I’d knew prior to arrival.
Reviewed on Aug. 30, 2025

Fidelity Hotel
Downtown Cleveland
Price was CA $918, price is now CA $835 per person
CA $835
per person
Oct 18 - Oct 20
found 6 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Cleveland (CLE)
9.6/10 Exceptional! (328 reviews)
Cleveland is working hard to sustain its revival, and the Fidelity is a good example of what the city can be.
Located in a side street running between the old Cleveland News-Herald building and Euclid Avenue it’s an easy walk to many of the city’s best known places, but it still feels like the retail shops that power a vibrant city center haven’t recovered enough to make the area fun and safe.
The Fidelity, however, does feel fun and safe: staff give you genuine welcoming smiles and are looking for ways to be helpful. The rooms are small, but comfortable with thoughtful touches like clothes steamers and pour-over kettles. The restaurant has a mercifully short menu of tasty food all available as room service. In the morning we had breakfast just outside the official seating area, which meant we could have our dog with us without breaking any rules.
Reviewed on Aug. 30, 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 $116 total
Oct 1 - Oct 2
includes taxes & fees

The Westin Cleveland Downtown
777 Saint Clair Ave Ne, Cleveland, OH
The price is CA $177 per night from Sep 14 to Sep 15
CA $177
CA $208 total
Sep 14 - Sep 15
includes taxes & fees

Hyatt Regency Cleveland At The Arcade
420 Superior Ave E, Cleveland, OH
The price is CA $191 per night from Sep 29 to Sep 30
CA $191
CA $224 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.