Chesterland Vacations from $249
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Latest Chesterland vacation packages
Price found within the past 48 hours. Click for updated prices.
Cedar Stables Inn and Suites
$249
per person
Sep 18 - Sep 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (549 reviews)
It took almost 40 minutes to find someone to check us in. Then when we got to our room both the sink and tub in the bathroom were backed up and full of hair and water that didn't belong to us. The room itself was pretty but the tub and sink shouldn't have had sitting water in them, it made me question how much the housekeeping actually cleaned between customers renting the property.
Reviewed on Aug 16, 2026
Landing Apartments near Rivergate Park Area
Cuyahoga Valley
$765
per person
Oct 9 - Oct 15
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.2/10 Wonderful! (9 reviews)
I had excellent communication with the corporate office and the on-site manager.
The building is fabulous with an excellent gym, rec room and pool. The garage is easy to get in and out, plus a brewery right next door...it was the perfect choice.
I will look for the company in other cities for future travels.
Reviewed on Jul 28, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chesterland
View all tripsStay near popular Chesterland attractions
Fowler's Mill Golf Course
8.0/10 (1 review)
This Pete Dye masterpiece challenges golfers with three distinct nine-hole courses woven through natural landscapes. Test your strategy on the Lake nine's signature Coastline hole where precision trumps power.
Berkshire Hill Golf Course
This former golf course wove through 240 acres of Ohio's natural hills, woods, and waterways. Players appreciated its strategic layout that balanced challenge with scenic tranquility.
Chesterland City Park
Chesterland City Park offers baseball fields, pickleball courts, and family-friendly pavilions. Reserve one of two covered areas for a premium picnic experience amid the park's recreational amenities.
Chester Town Hall
The administrative heart of Chester Township, this town hall hosts local government meetings and community events. Visitors can observe small-town governance in action during regular weekday business hours.
West Geauga Public Library
The Geauga West Library features a Digital Legacy Lab to convert analog media to digital formats. Browse the collection, enjoy the outdoor reading garden, or reserve a study room for focused work.
West Geauga Plaza
West Geauga Plaza serves as Chesterland's community hub with essential retail stores and local dining options. Enjoy a relaxed shopping experience at Giant Eagle or savor authentic cuisine at My Thai Restaurant.
Bessie Benner Metzenbaum Park
This 65-acre natural oasis features diverse habitats and a scenic creek for wildlife spotting. Explore accessible trails, then let children enjoy the nature-based playground while you relax at Wisteria Hill Shelter.
Silo Picnic Area
Silo Picnic Area offers a peaceful 1.4-acre space in Chesterland for walking and running through lush greenery. Bring your own charcoal for grilling and pack insect repellent in summer.
Chesterland Hotel Deals
The Westin Cleveland Downtown
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
$149 nightly
$175 total
Aug 23 - Aug 24
Total with taxes and fees
8.6/10 Excellent! (228 reviews)
"X"
Reviewed on Aug 19, 2026
Hotel Indigo Cleveland Downtown by IHG
651 Huron Rd E Cleveland OH
Fully refundable
$95 nightly
$112 total
Sep 7 - Sep 8
Total with taxes and fees
Crowne Plaza Cleveland at Playhouse Square by IHG
1260 Euclid Ave Cleveland OH
Fully refundable
$110 nightly
$129 total
Aug 23 - Aug 24
Total with taxes and fees
9/10 Wonderful! (1,399 reviews)
"Great location and easy to walk to Progressive Field and dining options"
Reviewed on Aug 19, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Chesterland vacation package cost?
Offering great value package deals from $249 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.
