Deals on vacations and trips to Chesterland

Save when you book Chesterland package deals

Choose two or more items and save on your trip:

Chesterland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Hotel Cleveland Downtown - Lakeside

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

4 out of 5
Downtown Cleveland
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 and free WiFi in public areas. A free area shuttle is offered as well.
Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Top Chesterland hotels deals

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
Get rates
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 snack bar/deli, dry cleaning, and free newspapers are also on offer.
Pet friendly
Free WiFi
Extended Stay America Premier Suites - Cleveland - Independence

Extended Stay America Premier Suites - Cleveland - Independence

2.5 out of 5
6025 Jefferson Dr, Independence, OH
Free Cancellation
Reserve now, pay when you stay
Get rates
A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. Luggage storage and a safe deposit box are also provided.
Breakfast included
Pet friendly
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
Get rates
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.
Spa
Pet friendly
Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

3 out of 5
1380 East 6th Street, Cleveland, OH
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and WiFi in public areas. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
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
Get rates
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
Holiday Inn Express Cleveland Downtown by IHG

Holiday Inn Express Cleveland Downtown by IHG

2.5 out of 5
629 Euclid Ave, Cleveland, OH
Free Cancellation
Get rates
A 24-hour gym, valet parking, and concierge services are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. There's luggage storage and multilingual staff can provide around-the-clock assistance.
Breakfast included
Free WiFi
Don't see what you're looking for?
See all available properties in Chesterland
View all properties
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

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

Berkshire Hill Golf Course

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

Berkshire Hill Golf Course

West Geauga Public Library

After visiting West Geauga Public Library, make a plan to see the other sights and activities in Chesterland.

West Geauga Public Library

Frequently asked questions

How much are vacation packages to Chesterland?
You can land a great hotel and flight bundle for as low as $323. 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

Photo by Kristin DePlatchett
Photo by Kristin DePlatchett