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.
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
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
8.2/10 Very Good! (1,004 reviews)
Met my expectations. Impressed with the shuttle service.

Reviewed on Mar. 10, 2025

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

4 out of 5
Downtown Cleveland
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Cleveland (CLE)
7.2/10 Good! (1,113 reviews)
Property is pretty old and limited food options around the hotel. Most restaurants are at least a 20 -30 min walk away.

Reviewed on Mar. 13, 2025

Residence Inn by Marriott Cleveland University Circle/Medical Center

Residence Inn by Marriott Cleveland University Circle/Medical Center

3 out of 5
Hough
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Cleveland (CLE)
8.8/10 Excellent! (717 reviews)
We loved our stay, clean, comfortable beds, spacious, great staff, easy parking-in and out, close to things. We will defiantly recommend your property. Thank you, from Detroit.

Reviewed on Mar. 8, 2025

ROOST Cleveland

ROOST Cleveland

4 out of 5
Downtown Cleveland
per person
May 25 - May 30
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Cleveland (CLE)
9.6/10 Exceptional! (386 reviews)
Nice place good customer service

Reviewed on Mar. 14, 2025

Barsala At The Monroe Apartments

Barsala At The Monroe Apartments

4 out of 5
University Circle
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Cleveland (CLE)
9/10 Wonderful! (20 reviews)
Nice place and great host

Reviewed on Jan. 29, 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
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Mar. 23 to Mar. 24
CA $185
CA $218 total
includes taxes & fees
Mar 23 - Mar 24
8.4/10 Very Good! (1,182 reviews)
"离会展中心近，比较方便，"

Reviewed on Mar. 11, 2025

The Westin Cleveland Downtown
Holiday Inn Cleveland Clinic by IHG
Holiday Inn Cleveland Clinic by IHG
3 out of 5
8650 Euclid Ave, Cleveland, OH
Fully refundable
The price is CA $193 per night from Mar. 28 to Mar. 29
CA $193
CA $226 total
includes taxes & fees
Mar 28 - Mar 29
8.6/10 Excellent! (1,013 reviews)
"The staff is extremely friendly and knowledgeable."

Reviewed on Mar. 14, 2025

Holiday Inn Cleveland Clinic by IHG
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 $148 per night from Mar. 24 to Mar. 25
CA $148
CA $174 total
includes taxes & fees
Mar 24 - Mar 25
8.4/10 Very Good! (1,108 reviews)
Quick Couples getaway
"We went for a quick couples trip to see the Cavs play. The convenient location made this ideal for us! We used their valet parking which was fast and seamless. The hotel was right next to restaurants which made it even better! The whole hotel was very clean and modern. Our room was spacious,very ..."

Reviewed on Mar. 12, 2025

Hotel Indigo Cleveland Downtown by IHG
See all 1,245 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 $997 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.