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.
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Price was $870, price is now $648 per person
$648
per person
May 11 - May 16
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Cleveland (CLE)
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. You'll appreciate the gym, bar/lounge, and laundry facilities.
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,313, price is now $901 per person
$901
per person
May 12 - May 19
just found
Roundtrip flight included
Houston (IAH) to Cleveland (CLE)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, laundry service, and valet parking. A coffee shop, a lobby fireplace, and WiFi in public areas are also on offer.
DoubleTree by Hilton Akron Fairlawn

DoubleTree by Hilton Akron Fairlawn

3 out of 5
Save 100% on your flight
Price was $1,122, price is now $788 per person
$788
per person
May 12 - May 19
just found
Roundtrip flight included
Houston (IAH) to Akron (CAK)
This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Landing Furnished Apartments Central Cleveland

Landing Furnished Apartments Central Cleveland

3 out of 5
Central
Price was $948, price is now $700 per person
$700
per person
May 12 - May 19
just found
Roundtrip flight included
Houston (IAH) to Cleveland (CLE)
A gym, self parking, and a virtual front desk are featured at this apartment. WiFi in public areas is free.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Save 100% on your flight
Price was $1,196, price is now $910 per person
$910
per person
May 12 - May 19
just found
Roundtrip flight included
Houston (IAH) to Cleveland (CLE)
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.

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
$106 nightly
The price is $125 total per night
$125 total
Apr 19 - Apr 20
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.
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne Cleveland OH
$109 nightly
The price is $128 total per night
$128 total
Apr 5 - Apr 6
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.
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
$118 nightly
The price is $139 total per night
$139 total
Apr 19 - Apr 20
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.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
8650 Euclid Ave Cleveland OH
Free Cancellation
$140 nightly
The price is $165 total per night
$165 total
May 1 - May 2
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.
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
2000 East Ninth Street Cleveland OH
Free Cancellation
$118 nightly
The price is $139 total per night
$139 total
Apr 9 - Apr 10
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, laundry service, and valet parking. A coffee shop, a lobby fireplace, and WiFi in public areas are also on offer.
Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
420 Superior Ave E Cleveland OH
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $170 total per night
$170 total
Apr 30 - May 1
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 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a lobby fireplace, and a hair salon are also on offer.
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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 $648. 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