Chesterland Vacations from $215

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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.
The Aurora Inn

The Aurora Inn

3 out of 5
Save 100% on your flight
Price was $313, price is now $215 per person
$215
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Akron (CAK)
9/10 Wonderful! (675 reviews)
We really enjoyed our stay. The restaurant was wonderful. The Inn was comfy and cozy. M

Reviewed on Jun 19, 2026

DoubleTree by Hilton Akron Fairlawn

DoubleTree by Hilton Akron Fairlawn

3 out of 5
Save 100% on your flight
Price was $510, price is now $347 per person
$347
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Akron (CAK)
8.6/10 Excellent! (820 reviews)
The location was perfect. I needed a late checkout and they were very accommodating. We ate lunch at the restaurant and it was delicious. The menu had many tasty options, it was hard to decide. As usual, the cookie was perfect!

Reviewed on Jun 14, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $1,052, price is now $723 per person
$723
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (901 reviews)
Front Desk Team Excelnt Bar and Returant Team did a great Job .

Reviewed on Jun 13, 2026

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $307, price is now $219 per person
$219
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,031 reviews)
Nice hotel and helpful staff and just across from Progressive Field.

Reviewed on Jun 19, 2026

Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $401, price is now $295 per person
$295
per person
Aug 21 - Aug 23
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (520 reviews)
Great reception, clean and good!

Reviewed on Jun 5, 2026

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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
$149 nightly
The price is $175 total per night from Jun 28 to Jun 29
$175 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (2,227 reviews)
"Staff was extremely helpful and friendly. Room was clean and looked like it had been recently remodeld. Shower door needed a new strip on the bottom to keep water in the shower and not all over the floor."

Reviewed on Jun 21, 2026

The Westin Cleveland Downtown
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
1100 Carnegie Ave Cleveland OH
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Jul 11 to Jul 12
$124 total
Jul 11 - Jul 12
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
"Nice hotel and helpful staff and just across from Progressive Field."

Reviewed on Jun 19, 2026

Hilton Garden Inn 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
$117 nightly
The price is $137 total per night from Jul 5 to Jul 6
$137 total
Jul 5 - Jul 6
Total with taxes and fees
8.4/10 Very Good! (1,737 reviews)
"Very clean and close to Rock and Roll hall of fame. We attempted to go to dinner at the restaurant one evening and it was closed due to some electrical issue? We told the front desk person we were looking for a restaurant where we could get a salad, she sent us to a pub down the street that just ..."

Reviewed on Jun 20, 2026

Hotel Indigo Cleveland Downtown by IHG
See all 1,556 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.

Find the Best Chesterland Vacation Packages

Chesterland Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Fowlers Mill Golf Course and Chardon Lakes Golf Club

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Frequently asked questions

How much does a Chesterland vacation package cost?
Offering great value package deals from $215 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.