Chesterland Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Chesterland

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 S$189 per night from 11 Dec to 12 Dec
S$189
includes taxes & fees
11 Dec - 12 Dec
9.4/10 Exceptional! (2,337 reviews)
"Beautiful building & good location. Room was clean except for carpet & chair. Carpet really needs a good clean as does the chair. Outside of window also very dirty. Elevator doors also need cleaned on inside. Staff, including valet, were very nice & did a great job. Thank you!"

Reviewed on 29 Nov,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 S$186 per night from 22 Dec to 23 Dec
S$186
includes taxes & fees
22 Dec - 23 Dec
8.4/10 Very Good! (1,003 reviews)
"Clean, comfortable and friendly staff. Great option and reasonably priced."

Reviewed on 25 Nov,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 S$106 per night from 25 Dec to 26 Dec
S$106
includes taxes & fees
25 Dec - 26 Dec
7.4/10 Good! (1,351 reviews)
"Staff were wonderful. Hotel was acceptable. Hard to get hot water, had to get a coffee pot from front desk, none in room. $100 security deposit up front tells you that this hotel may have some issues. Rooms good size and comfortable, but all accessories have to come from front desk."

Reviewed on 29 Nov,2024

Extended Stay America Premier Suites - Cleveland - Independence
See all 1,216 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.

Frequently asked questions

How much does a Chesterland holiday package cost?
Starting from only , a holiday 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 holiday?
Savvy travellers 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 holiday.
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 organising an upscale romantic escape or a budget family adventure, browse our package deals today.
Can I choose my airline with a Chesterland Expedia holiday package?
With a holiday 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 holiday package?
Whether it’s your hotel, flight or rental car, you can cancel or change it. Locked in your Chesterland holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.