Chesterland Vacations from $246

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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.

The Latest Chesterland vacation packages

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
Oct 31 - Nov 3
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Cleveland (CLE)
8.8/10 Excellent! (1,002 reviews)
Easy on and off highway. Lots of food choices, not far from Cleveland, breakfast is standard for Hampton.

Reviewed on Jul 29, 2025

The Willoughby House

The Willoughby House

3 out of 5
per person
Sep 19 - Sep 21
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
10/10 Exceptional! (2 reviews)
Beautiful property. Nice location. Excellent lounge & restaurant.

Reviewed on Aug 4, 2025

Fidelity Hotel

Fidelity Hotel

4 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Sep 19 - Sep 21
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (291 reviews)
This is a fabulous boutique hotel with friendly service near all.

Reviewed on Aug 9, 2025

Hampton Inn Cleveland-Downtown

Hampton Inn Cleveland-Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Sep 23 - Sep 28
just found
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,372 reviews)
Issues were resolved at checkout

Reviewed on Aug 9, 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Sep 23 - Sep 28
just found
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.6/10 Excellent! (1,012 reviews)
The street view is nice, but there is a reason that there is complimentary ear plugs. Tremendous amounts of noise at night. Friday night was horrible

Reviewed on Aug 9, 2025

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Discover the most popular places to visit in Chesterland

Fowler's Mill Golf Course

4/5(1 review)

Enjoy a round of golf in Chesterland at Fowler's Mill Golf Course. While in this quaint area, you can savor the top-notch restaurants.

Fowler's Mill Golf Course

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
$129 nightly
The price is $152 total per night from Aug 21 to Aug 22
$152 total
Aug 21 - Aug 22
Total includes taxes and fees
8.4/10 Very Good! (1,493 reviews)
"Nice hotel, big rooms, friendly staff. Would stay again"

Reviewed on Aug 7, 2025

The Westin Cleveland Downtown
Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
420 Superior Ave E, Cleveland, OH
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Sep 1 to Sep 2
$153 total
Sep 1 - Sep 2
Total includes taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Totally amazing building — a true architectural gem. We were a little astonished actually by the remarkable interior. Good, polite staff . . . everything fine. View from our window wasn’t great, but it’s okay. We weren’t in the room much anyway. Very cool that the staff wore Cleveland Guardians jerseys! ..."

Reviewed on Aug 9, 2025

Hyatt Regency Cleveland At The Arcade
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
$112 nightly
The price is $132 total per night from Aug 24 to Aug 25
$132 total
Aug 24 - Aug 25
Total includes taxes and fees
8.4/10 Very Good! (1,265 reviews)
"Great dining , clean and cute room"

Reviewed on Aug 7, 2025

Hotel Indigo Cleveland Downtown by IHG
See all 1,460 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.

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Frequently asked questions

How much does a Chesterland vacation package cost?
Offering great value package deals from $246 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?
January, April and September are the best times to search for cheap Chesterland vacation packages. Choosing to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Chesterland?
The ideal duration for your Chesterland vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to tick off all the leading attractions and explore some hidden treasures 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.
Does Expedia offer Book Now, Pay Later Chesterland vacation packages?
Your Chesterland trip is meant to be an escape from your busy life, not a reason for money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.