Deals on vacations and trips to Chesterland

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Chesterland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Highlander Inn Cleveland Beachwood Near I-480

Highlander Inn Cleveland Beachwood Near I-480

2.5 out of 5
Price was $535, price is now $389 per person
$389
per person
Aug 10 - Aug 17
found 13 hours ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. A communal living room, express check-out, and dry cleaning are also on offer.
Dav-Ed Motel

Dav-Ed Motel

2.5 out of 5
Price was $1,145, price is now $746 per person
$746
per person
Jul 22 - Jul 27
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.
The Inn at Fulton

The Inn at Fulton

2 out of 5
Save 100% on your flight
Price was $1,303, price is now $862 per person
$862
per person
Aug 10 - Aug 17
found 13 hours ago
Roundtrip flight included
New York (JFK) to Cleveland (CLE)
This aparthotel includes free WiFi in public areas and laundry facilities.
The Inn at Woodsong Acres

The Inn at Woodsong Acres

3 out of 5
Price was $1,541, price is now $1,108 per person
$1,108
per person
Jul 22 - Jul 27
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Cleveland (CLE)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Barbecue grills are provided for your convenience.
Bertram Inn at Glenmoor

Bertram Inn at Glenmoor

3.5 out of 5
Save 100% on your flight
Price was $1,380, price is now $996 per person
$996
per person
Aug 4 - Aug 8
found 19 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Akron (CAK)
This hotel features a golf course, a full-service spa, and 3 restaurants. Enjoy the 6 outdoor tennis courts and perks like free valet parking and free WiFi. Enjoy the gym and unwind at the bar/lounge and poolside bar.

Top Chesterland hotels deals

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
651 Huron Rd E Cleveland OH
Free Cancellation
$122 nightly
The price is $143 total per night
$143 total
May 27 - May 28
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Free WiFi
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne Cleveland OH
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $152 total per night
$152 total
May 24 - May 25
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
Hotel Cleveland, Autograph Collection

Hotel Cleveland, Autograph Collection

4 out of 5
24 Public Sq Cleveland OH
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $163 total per night
$163 total
May 28 - May 29
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Self parking is offered and multilingual staff can provide around-the-clock assistance.
Free WiFi
Restaurant
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
1100 Carnegie Ave Cleveland OH
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $124 total per night
$124 total
May 27 - May 28
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. A bar/lounge, a 24-hour front desk, and a fireplace in the lobby are also provided.
Pool
Pet friendly
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
8650 Euclid Ave Cleveland OH
Free Cancellation
$144 nightly
The price is $169 total per night
$169 total
May 24 - May 25
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the sauna, bar/lounge, and laundry facilities.
Pool
Free WiFi
Wyndham Independence

Wyndham Independence

4 out of 5
6200 Quarry Lane Independence OH
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $74 total per night
$74 total
May 27 - May 28
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 11 conference rooms, free WiFi in public areas, and express check-out. Enjoy the 24-hour gym and perks like free self parking.
Pool
Hot Tub
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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.

Popular places to visit

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.

Fowler's Mill Golf Course

Berkshire Hill Golf Course

Enjoy a round of golf in Chesterland at Berkshire Hill Golf Course.

Berkshire Hill Golf Course

West Geauga Plaza

You can search for that perfect souvenir at West Geauga Plaza during your stay in Chesterland.

West Geauga Plaza

Frequently asked questions

How much are vacation packages to Chesterland?
You can land a great hotel and flight bundle for as low as $389. With one of our Travelocity vacation packages, a visit to Chesterland has never looked so enticing! Save your time and cash and get an early start with packing your suitcases.
Where can I get the best vacation package deals for Chesterland?
Landing a great package deal to Chesterland is a breeze with Travelocity. With 400 partner airlines and 1,000,000 properties around the world, the choice is yours when selecting your hotels and flights.
Why should I book my Chesterland vacation package via Travelocity?
Because you'll never wander alone if you book your vacation with us, and we offer round-the-clock support and top-quality service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to choose from. It's our job to make your daydreams a reality.
Will I save money on my Chesterland car rental if I bundle it with a hotel or flight?
Combining your flight, hotel and car into a Chesterland vacation package is an excellent way to land the best prices. Plus, having your own rental car gives you the freedom to make your way to all those landmarks you want to check out. Sitting 40 mi away from Chesterland, Smolen-Gulf Covered Bridge is one place that should be on your to-do list. Buckle up and make a day trip of it.
Which airport is best for Chesterland?
One top option is Hopkins Intl. Airport (CLE). From here, you'll need to travel east for roughly 25 mi to reach downtown Chesterland. Another possibility is Akron-Canton Airport (CAK), which is 40 mi away from central Chesterland.

Photos of local treasures

Browse Chesterland vacation photos for more inspiration

Chesterland, Ohio, USA - 2-21-22: A small bridge in the Bessie Benner Metzenbaum Park
Chesterland