Chesterland Vacation Packages

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Photo by Kristin DePlatchett
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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.

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 $172 per night from Jun. 16 to Jun. 17
CA $172
CA $202 total
includes taxes & fees
Jun 16 - Jun 17
9.4/10 Exceptional! (2,114 reviews)
"This hotel is stunningly beautiful. It’s was a school board building that was restored its original glory. The staff is friendly and helpful. Additionally, it’s within walking distance to almost every attraction in the downtown area. We loved staying there, and if we go back to Cleveland, we will ..."

Reviewed on Jun. 1, 2024

Drury Plaza Hotel Cleveland Downtown
DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside
DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside
4 out of 5
1111 Lakeside Avenue E, Cleveland, OH
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Jun. 24 to Jun. 25
CA $189
CA $222 total
includes taxes & fees
Jun 24 - Jun 25
7.2/10 Good! (1,009 reviews)
"The carpets need cleaning."

Reviewed on May 31, 2024

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside
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 $117 per night from Jun. 4 to Jun. 5
CA $117
CA $137 total
includes taxes & fees
Jun 4 - Jun 5
7.4/10 Good! (1,081 reviews)
"It was nice"

Reviewed on May 26, 2024

Extended Stay America Premier Suites - Cleveland - Independence
See all 1,129 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

Family Vacations

Frequently asked questions

How much does a Chesterland vacation package cost?
Starting from only , 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.

Discover the most popular places to visit in Chesterland

Image for Fowler's Mill Golf Course

Fowler's Mill Golf Course

Enjoy a round of golf in Chesterland at Fowler's Mill Golf Course. While in this quaint area, you can savor the top-notch restaurants.

Fowler's Mill Golf Course

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.