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.
Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
per person
Jun. 24 - Jun. 26
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (314 reviews)
Love how quiet the hotel was even though it was super busy!

Reviewed on Apr. 14, 2024

The Abbey Apartments By Barsala

The Abbey Apartments By Barsala

4 out of 5
Tremont
per person
Jun. 20 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (21 reviews)
The property at that time was very new.

Reviewed on May 3, 2024

Explorer Rest & Recreation

Explorer Rest & Recreation

2 out of 5
per person
Jun. 24 - Jun. 26
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9.2/10 Wonderful! (55 reviews)
Came for our grandson's baseball tournament down the road, and didn't want to stay at the large hotel/water park down the road. This re-done motel exceeded our expectations! Nice size rooms, all expected amenities, beds, pillows and linens like heaven! Only thing I can think to recommend is to include at least one luggage rack. There are no dressers or closets in the room, so opening and closing suitcases on the bed every time something was needed got a little tedious.

Reviewed on May 12, 2024

ROOST Cleveland

ROOST Cleveland

4 out of 5
Downtown Cleveland
per person
Jun. 20 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9.6/10 Exceptional! (221 reviews)
Very clean and beautiful apartment. Near many restaurants and attractions. I would definitely recommend.

Reviewed on Mar. 28, 2024

Hotel Kilbourne

Hotel Kilbourne

2.5 out of 5
Historic Downtown Sandusky
per person
Jun. 24 - Jun. 26
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9.2/10 Wonderful! (489 reviews)
Super cute hotel in Sandusky. Will definitely be back.

Reviewed on Apr. 23, 2024

Chesterland Hotel Deals

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 $116 per night from Jun. 6 to Jun. 7
CA $116
CA $137 total
includes taxes & fees
Jun 6 - Jun 7
7.6/10 Good! (1,111 reviews)
"I would Definetly stay here again"

Reviewed on May 14, 2024

Extended Stay America Premier Suites - Cleveland - Independence
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 May 23 to May 24
CA $172
CA $202 total
includes taxes & fees
May 23 - May 24
9.4/10 Exceptional! (2,085 reviews)
"I always enjoy staying at the Drury. It is in a cool building that used to be the 1920 Cleveland Board of Education Building, and has the free breakfast and 5:30 kickback. My only issue this time was the room cleanliness. The edges around the room had dirt, crumbs, and even a straw. It bothered me ..."

Reviewed on May 13, 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 $166 per night from May 24 to May 25
CA $166
CA $196 total
includes taxes & fees
May 24 - May 25
7.2/10 Good! (1,000 reviews)
"Very nice hotel located within walking distance of the Rock & Roll Hall of Fame. Staff were so nice and friendly."

Reviewed on May 13, 2024

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside
See all 1,144 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.

Explore other types of vacation packages

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 CA $740, 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.