Chesterland Vacations from $319
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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.
Kimpton Schofield Hotel by IHG
Downtown Cleveland
Price was $460, price is now $319 per person
$319
per person
Dec 20 - Dec 22
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
8.6/10 Excellent! (1,015 reviews)
We love the Kimpton. We stay here often. Always clean and very friendly.
Reviewed on Oct 12, 2025
Fidelity Hotel
Downtown Cleveland
Price was $541, price is now $374 per person
$374
per person
Dec 20 - Dec 22
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
9.6/10 Exceptional! (368 reviews)
Very pet friendly; however quick access to grass was farther than anticipated.
Property was beautifully appointed with 1920’s decor! Loved it!
Reviewed on Oct 12, 2025
Cleveland Marriott Downtown at Key Tower
Downtown Cleveland
Price was $552, price is now $410 per person
$410
per person
Dec 20 - Dec 22
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
8.8/10 Excellent! (1,001 reviews)
like to give a shout out to the bell service during a game weekend. they were friendly and FAST acting on Valet and bag pick up.
Reviewed on Sep 26, 2025
Comfort Suites Twinsburg
Price was $602, price is now $458 per person
$458
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Cleveland (CLE)
7.6/10 Good! (783 reviews)
The shower head in the bathroom of room 220 needs a major cleaning. It's black and moldy.
Reviewed on Oct 3, 2025
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View all tripsDiscover the most popular places to visit in Chesterland
Fowler's Mill Golf Course
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.
Chesterland Hotel Deals
The Westin Cleveland Downtown
777 Saint Clair Ave Ne, Cleveland, OH
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Oct 31 to Nov 1
$149 total
Oct 31 - Nov 1
Total with taxes and fees
8.4/10 Very Good! (1,666 reviews)
"Great locution we enjoyed this day"
Reviewed on Oct 10, 2025
Wyndham Independence
6200 Quarry Lane, Independence, OH
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Oct 31 to Nov 1
$78 total
Oct 31 - Nov 1
Total with taxes and fees
6.4/10 (1,025 reviews)
"I love love this hotel. I’m not gonna pick out the little things because overall they were great!! BUT…… though most hotels do the $100 hold, some don’t. And those that do take the hold, should specify it boldly during payout. A customer shouldn’t find out they have to pay more or need more once ..."
Reviewed on Oct 9, 2025
Kimpton Schofield Hotel by IHG
2000 East Ninth Street, Cleveland, OH
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $135 total per night from Oct 16 to Oct 17
$135 total
Oct 16 - Oct 17
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
"Comfortable beds and good water pressure. Staff was friendly and helpful. Location is in the middle of everything."
Reviewed on Oct 6, 2025
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.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
