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.
Highlander Inn Cleveland Beachwood Near I-480

Highlander Inn Cleveland Beachwood Near I-480

2.5 out of 5
Price was $166, price is now $133 per person
$133
per person
Dec 12 - Dec 14
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room, dry cleaning, and luggage storage are also on offer.
Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was $554, price is now $410 per person
$410
per person
Dec 31 - Jan 3
found 3 hours ago
Roundtrip flight included
Orlando (MCO) 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
Price was $501, price is now $377 per person
$377
per person
Dec 31 - Jan 3
found 3 hours ago
Roundtrip flight included
Orlando (MCO) 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.
InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $666, price is now $520 per person
$520
per person
Dec 31 - Jan 3
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Cleveland (CLE)
This luxury hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. WiFi in public areas is free. Valet parking, a terrace, and a lobby fireplace are also offered.
Wyndham Avon

Wyndham Avon

3.5 out of 5
Save 100% on your flight
Price was $280, price is now $223 per person
$223
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like 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
$129 nightly
The price is $152 total per night
$152 total
Nov 22 - Nov 23
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
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
$67 nightly
The price is $79 total per night
$79 total
Nov 24 - Nov 25
Total with taxes and fees
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
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
$95 nightly
The price is $112 total per night
$112 total
Nov 23 - Nov 24
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, a computer station, and luggage storage are also on offer.
Pet friendly
Free WiFi
Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

4 out of 5
1380 East 6th Street Cleveland OH
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $180 total per night
$180 total
Nov 8 - Nov 9
Total with taxes and fees
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
Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
420 Superior Ave E Cleveland OH
$145 nightly
The price is $170 total per night
$170 total
Nov 19 - Nov 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 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
Hilton Cleveland Downtown

Hilton Cleveland Downtown

4 out of 5
100 Lakeside Ave East Cleveland OH
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $163 total per night
$163 total
Nov 22 - Nov 23
Total with taxes and fees
The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. A restaurant, a 24-hour front desk, and a coffee shop are also provided.
Pool
Pet friendly
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.

Stay near popular Chesterland attractions

Fowler's Mill Golf Course

8.0/10 (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.
See properties

Frequently asked questions

How much are vacation packages to Chesterland?
You can land a great hotel and flight bundle for as low as $133. 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

A wooden bridge over a snow-covered path in a forest.
A pile of small orange pumpkins with stems.