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.
Baymont by Wyndham Harvard

Baymont by Wyndham Harvard

2.5 out of 5
per person
Dec. 26 - Dec. 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Akron (CAK)
6.2/10 (321 reviews)
The manager on duty was rude and uncaring. We had people next door who were shouting and swearing and sounded intoxicated. And the man threw his phone at his female partner. She was crying. We didn’t feel safe and the manager/desk clerk refused to move us to another room. He said “I talked to him and he said he’d be quiet”. I went back to my room and the shouting continued. I went back to the manager and he finally agreed to move us after I insisted. We did not feel safe, but as we were moving, the manager said “he wouldn’t have hurt you.” The manager also said to me “haven’t you ever stayed at a motel before?” I replied that I had stayed at hotels all over the world and never experienced this. He kind of huffed and said “really?” I replied really. We will never stay at this hotel again!

Reviewed on Oct. 29, 2024

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Chesterland Hotel Deals

Drury Plaza Hotel Cleveland Downtown
Drury Plaza Hotel Cleveland Downtown
3 out of 5
1380 East 6th Street, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Nov. 19 to Nov. 20
CA $168
CA $197 total
includes taxes & fees
Nov 19 - Nov 20
9.4/10 Exceptional! (2,311 reviews)
"5 star hotel at 3 star price."

Reviewed on Nov. 13, 2024

Drury Plaza Hotel Cleveland Downtown
The Westin Cleveland Downtown
The Westin Cleveland Downtown
4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Nov. 26 to Nov. 27
CA $167
CA $196 total
includes taxes & fees
Nov 26 - Nov 27
8.4/10 Very Good! (1,001 reviews)
"Guest service was nice and I was able to check in very early. They were very accomadating"

Reviewed on Nov. 11, 2024

The Westin Cleveland Downtown
Extended Stay America Premier Suites - Cleveland - Independence
Extended Stay America Premier Suites - Cleveland - Independence
2.5 out of 5
6025 Jefferson Dr, Independence, OH
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Dec. 8 to Dec. 9
CA $99
CA $117 total
includes taxes & fees
Dec 8 - Dec 9
7.4/10 Good! (1,334 reviews)
"Really great service"

Reviewed on Nov. 11, 2024

Extended Stay America Premier Suites - Cleveland - Independence
See all 1,201 properties in Chesterland
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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Frequently asked questions

How much does a Chesterland vacation package cost?
Starting from only CA $513, a vacation package is your portal to inexpensive travel. Custom build your Chesterland trip by picking from our comprehensive range of hotels, airfares and rental cars.
How do I get a cheap travel package to Chesterland?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got it all. Pick a combination that suits you and watch your savings stack up. Of course, a package deal is never one-size-fits-all. That’s why we offer over 550 air carriers and 1,000,000 hotel options around the globe, which lets you customize your Chesterland getaway.
How far in advance should I book my Chesterland vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can usually browse through international airfares on Expedia up to 12 months before your flight. If you’ve left booking to the last minute, don’t despair. Budget prices occasionally occur just weeks before departure.
What does an Expedia Chesterland travel package include?
Car rentals, hotels and flights — we bring you the best deals. All you’ll have to do is decide on your preferred combination. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it simple to put together an unforgettable Chesterland vacation.
What should I know before booking a Chesterland travel package?
You’ll enjoy excellent savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything together simply makes planning easier. So why waste money or time? Whether you’re organizing an upscale romantic escape or a budget family adventure, browse our package deals today.
Can I choose my airline with a Chesterland Expedia vacation package?
With a vacation package, you’re the boss. Whether you’re hoping to fly to Chesterland in economy or business class, simply choose from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Chesterland vacation package?
Whether it’s your hotel, flight or rental car, you can cancel or change it. Locked in your Chesterland vacation package in the last 24 hours? You may be able to make any changes for free. If it’s been longer than that, you may be charged a fee by your airline, hotel or car rental company. For more details, take a look at our Customer Service Portal. We’re here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.