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.
Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
per person
Sep 6 - Sep 9
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
It was the perfect location from Cleveland and the national park. It was a mix of nature and city all with a central landing place on our trip.

Reviewed on Jul. 11, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
per person
Sep 6 - Sep 9
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Cleveland (CLE)
8.6/10 Excellent! (1,001 reviews)
Loved my stay! Was pretty loyal to Marriot brands but IHG is doing it right. Actually switched my next trip hotel to an IHG property.

Reviewed on Jul. 12, 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Sep 6 - Sep 9
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Cleveland (CLE)
8.6/10 Excellent! (1,442 reviews)
Parking wasn't good..cant go in and out if you park in structure ir you will be charged I was told by front desk. Gotced to valet for more money.

Reviewed on Jul. 9, 2025

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
per person
Sep 6 - Sep 9
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
Great place to visit

Reviewed on Jul. 8, 2025

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
per person
Sep 6 - Sep 9
found 18 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Cleveland (CLE)
8.8/10 Excellent! (1,131 reviews)
Be aware since I didn't see it listed anywhere that this is a VALET only parking hotel. There is no regular parking. This does make it tough when you're on a time constraint BUT that being said the hotel was nice, the staff was great.

Reviewed on Jul. 10, 2025

Ready to book your vacation to Chesterland?

 

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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 $204 per night from Jul 31 to Aug 1
CA $204
CA $240 total
Jul 31 - Aug 1
includes taxes & fees
8.4/10 Very Good! (1,447 reviews)
Great trip
"Everything was amazing."

Reviewed on Jul. 11, 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 $152 per night from Aug 4 to Aug 5
CA $152
CA $179 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,194 reviews)
"Didn’t like no pool or microwave in room"

Reviewed on Jul. 9, 2025

Hotel Indigo Cleveland Downtown by IHG
Crowne Plaza Cleveland at Playhouse Square by IHG
Crowne Plaza Cleveland at Playhouse Square by IHG
3.5 out of 5
1260 Euclid Ave, Cleveland, OH
Fully refundable
The price is CA $152 per night from Aug 4 to Aug 5
CA $152
CA $179 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (1,181 reviews)
"Great location downtown. Very friendly staff. Room was new and modern. Very clean"

Reviewed on Jul. 9, 2025

Crowne Plaza Cleveland at Playhouse Square by IHG
See all 1,349 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?
You'll find cheap prices from CA $534 on Expedia for your Chesterland escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Chesterland costs.
What are the cheapest months to go to Chesterland?
You can typically find lower rates and greater availability in January, February and November. Browse our cheap Chesterland vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesterland?
Typically, a handful of days is enough to check out the top attractions during your Chesterland vacation. But if you want to have more time to unwind or take day trips, think about extending your trip.
How to find the best Chesterland package deals?
Bagging a cheap Chesterland package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most affordable Chesterland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterland vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Chesterland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chesterland?
If you've got your Chesterland vacation dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Chesterland?

  1. Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Chesterland.
  2. Set a budget: Consider costs like flights, food and transportation when calculating how much to put aside for your trip to Chesterland. Then, pick a property that fits your budget, whether that's an economical option or a swankier getaway.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Chesterland. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Chesterland vacation package.

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