Chesterland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton

The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton

4 out of 5
University Circle
per person
Mar. 3 - Mar. 7
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Cleveland (CLE)
8.2/10 Very Good! (1,003 reviews)
Stayed many times and pleased with price and staff!

Reviewed on Jan. 6, 2025

The Orbit Hotel, Trademark Collection by Wyndham

The Orbit Hotel, Trademark Collection by Wyndham

2.5 out of 5
per person
Mar. 19 - Mar. 26
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
9.2/10 Wonderful! (1,247 reviews)
Great property is very convenient

Reviewed on Jan. 8, 2025

Hampton Inn Cleveland-Westlake

Hampton Inn Cleveland-Westlake

2.5 out of 5
per person
Mar. 19 - Mar. 26
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
8.2/10 Very Good! (1,001 reviews)
Simple/basic room, clean and comfortable. Warm breakfast and friendly staff.

Reviewed on Dec. 29, 2024

JARVIS Edgewater Park & Beach 5BD Villa

JARVIS Edgewater Park & Beach 5BD Villa

3.5 out of 5
Edgewater
Save 100% on your flight
per person
Mar. 26 - Mar. 29
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
No reviews
Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
per person
Mar. 19 - Mar. 26
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
9/10 Wonderful! (1,007 reviews)
Recently updated and clean place to stay with fair prices.

Reviewed on Jan. 7, 2025

Ready to book your vacation to Chesterland?

 

Choose your dates

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 Jan. 16 to Jan. 17
CA $172
CA $203 total
includes taxes & fees
Jan 16 - Jan 17
9.4/10 Exceptional! (2,369 reviews)
"Fun atmosphere for New Years Eve"

Reviewed on Jan. 6, 2025

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 $171 per night from Jan. 13 to Jan. 14
CA $171
CA $201 total
includes taxes & fees
Jan 13 - Jan 14
8.4/10 Very Good! (1,064 reviews)
"Very close to the venue"

Reviewed on Jan. 6, 2025

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 $97 per night from Feb. 4 to Feb. 5
CA $97
CA $114 total
includes taxes & fees
Feb 4 - Feb 5
7.4/10 Good! (1,404 reviews)
"It was plowed"

Reviewed on Jan. 6, 2025

Extended Stay America Premier Suites - Cleveland - Independence
See all 1,230 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?
Offering great value package deals from CA $916 on Expedia, you’ll be pleasantly surprised at how much a vacation to Chesterland costs! Expedia’s packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesterland?
You can usually find reduced prices and better availability in January, February and November. Check out our cheap Chesterland vacation packages and you could score some great off-season deals.
How many days is enough for Chesterland?
The ideal duration for your Chesterland vacation depends on what you’d like to do. Generally, a handful of days to a week will give you enough time to tick off all the leading sights and explore some hidden spots along the way.
How to find the best Chesterland package deals?
Begin your search for a Chesterland package deal by entering your travel dates and destination under our “Packages” tab. Then add some filters, like “Popular locations” and “Amenities,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and browse offers that come with big savings. If you don’t find the perfect Chesterland package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chesterland escape underway.
Is it cheaper to book a Chesterland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You’ll generally score a better deal than booking each component individually. And you’ll still have the flexibility to create a tailored Chesterland vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Chesterland?
If you’re considering an impromptu Chesterland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterland?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the available activities will also help you decide when to visit Chesterland.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your hotel will probably be the largest expense during your trip to Chesterland.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to get to in Chesterland. Then, estimate how long you’ll need at each, along with any travel time.
  4. Combine your airfare and accommodations: Once you’ve nailed down your trip dates and duration, lock in the perfect Chesterland vacation package for you.

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