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.
Crowne Plaza Cleveland Airport by IHG

Crowne Plaza Cleveland Airport by IHG

3.5 out of 5
per person
Jul. 16 - Jul. 18
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
7.6/10 Good! (985 reviews)
The hotel was convenient for a stip enroute to Chicago from Maryland. Pool could have been a bit warmer. Staff was VERY nice. A cute bar in the basement and Becky was an excellent host.

Reviewed on Mar. 21, 2025

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

4 out of 5
Downtown Cleveland
per person
Jun. 8 - Jun. 12
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Cleveland (CLE)
7.2/10 Good! (1,126 reviews)
Very clean and staff was awesome!

Reviewed on Apr. 11, 2025

The Abbey Apartments By Barsala

The Abbey Apartments By Barsala

3.5 out of 5
Tremont
per person
Jun. 23 - Jun. 27
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Cleveland (CLE)
8.6/10 Excellent! (83 reviews)
The place was clean and neat, clean towels and bedding and with no clutter. I appreciate the extra towels and washer and dryer available in the unit. Would recommend!

Reviewed on Apr. 13, 2025

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
per person
May 27 - May 29
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Cleveland (CLE)
7.4/10 Good! (1,001 reviews)
The staff were wonderful, the room clean, the breakfast was fantastic! Parking was easy and I will stay here again!

Reviewed on Apr. 10, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
per person
May 27 - May 29
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Cleveland (CLE)
8.6/10 Excellent! (1,203 reviews)
The staff was amazing, room was clean and comfortable. Lots of dining within walking distance of the hotel.

Reviewed on Apr. 19, 2025

Ready to book your vacation to Chesterland?

 

Choose your dates

Chesterland Hotel Deals

The Westin Cleveland Downtown
The Westin Cleveland Downtown
4 out of 5
777 Saint Clair Ave Ne, Cleveland, OH
The price is CA $151 per night from Apr. 24 to Apr. 25
CA $151
CA $177 total
includes taxes & fees
Apr 24 - Apr 25
8.4/10 Very Good! (1,255 reviews)
"The staff was amazing, room was clean and comfortable. Lots of dining within walking distance of the hotel."

Reviewed on Apr. 19, 2025

The Westin Cleveland Downtown
Hotel Indigo Cleveland Downtown by IHG
Hotel Indigo Cleveland Downtown by IHG
3.5 out of 5
651 Huron Rd E, Cleveland, OH
Fully refundable
The price is CA $143 per night from Apr. 24 to Apr. 25
CA $143
CA $168 total
includes taxes & fees
Apr 24 - Apr 25
8.4/10 Very Good! (1,115 reviews)
"Good hotel overall. The bathroom was very small in the room I stayed."

Reviewed on Apr. 17, 2025

Hotel Indigo Cleveland Downtown by IHG
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 $166 per night from May 5 to May 6
CA $166
CA $195 total
includes taxes & fees
May 5 - May 6
9.4/10 Exceptional! (2,439 reviews)
"Beautiful hotel close to Rock and Roll Hall of Fame. It’s great they provide a good breakfast (they also provide food for dinner) because there are not a lot of dining options in the era, even if the Starbucks/Dunkin variety. Friendly staff and great bar in hotel."

Reviewed on Apr. 19, 2025

Drury Plaza Hotel Cleveland Downtown
See all 1,312 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 $729 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.