Deals on vacations and trips to Chester

Save when you book Chester package deals

Choose two or more items and save on your trip:

Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Aspen Select

Aspen Select

3.5 out of 5
Kutzky Park
Price was $609, price is now $535 per person
$535
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Traverse City (TVC) to Rochester (RST)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a terrace are also provided.
The Towers At Kahler Grand Hotel

The Towers At Kahler Grand Hotel

4 out of 5
Downtown Rochester
Price was $1,029, price is now $910 per person
$910
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Traverse City (TVC) to Rochester (RST)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Relax with a drink at the bar/lounge and enjoy the free self-serve breakfast each morning.
The Berkman

The Berkman

3 out of 5
Folwell
Price was $682, price is now $619 per person
$619
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Traverse City (TVC) to Rochester (RST)
This aparthotel features a gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free WiFi. Self parking, a 24-hour business center, and a terrace are also offered.
Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

3 out of 5
Kutzky Park
Price was $681, price is now $618 per person
$618
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Traverse City (TVC) to Rochester (RST)
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and WiFi in public areas. Self parking, a 24-hour business center, and a terrace are also offered.
Kahler Grand Hotel

Kahler Grand Hotel

3 out of 5
Downtown Rochester
Price was $662, price is now $614 per person
$614
per person
Apr 7 - Apr 9
found 8 hours ago
Roundtrip non-stop flight included
Traverse City (TVC) to Rochester (RST)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Top Chester hotels deals

AmericInn by Wyndham Osage

AmericInn by Wyndham Osage

2.5 out of 5
2212 Highway 218 Osage IA
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $102 total per night
$102 total
Mar 12 - Mar 13
Total with taxes and fees
This hotel features an indoor pool and a 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.
Pool
Hot Tub
Super 8 by Wyndham Cresco IA

Super 8 by Wyndham Cresco IA

2 out of 5
511 Second Ave SE, Hwy 9 & 5th Street Cresco IA
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $73 total per night
$73 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly
Country Trails Inn & Suites

Country Trails Inn & Suites

2 out of 5
809 U.S. 52 Preston MN
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $140 total per night
$140 total
Feb 19 - Feb 20
Total with taxes and fees
An attached winery and an indoor pool are featured at this smoke-free hotel. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas and a fireplace in the lobby are also provided.
Pool
Hot Tub
Americas Best Value Inn & Suites Spring Valley

Americas Best Value Inn & Suites Spring Valley

2 out of 5
745 N Broadway St Spring Valley MN
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $94 total per night
$94 total
Feb 19 - Feb 20
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and laundry facilities and free newspapers are also offered.
Western Inn & Suites

Western Inn & Suites

2 out of 5
1530 Main St, Osage IA
Free Cancellation
Reserve now, pay when you stay
$63 nightly
The price is $71 total per night
$71 total
Feb 19 - Feb 20
Total with taxes and fees
The motel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
Oak Meadow Farmhouse

Oak Meadow Farmhouse

Spring Valley MN
$300 nightly
The price is $322 total per night
$322 total
Feb 19 - Feb 20
Total with taxes and fees
This farm stay features laundry facilities.
Don't see what you're looking for?
See all available properties in Chester
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.

Frequently asked questions

How much are vacation packages to Chester?
Travelocity has package deals to Chester, including flights and hotels, starting from as low as $535. With all the extra money, you could throw in some cool tours or maybe also add some extra days to your exciting getaway.
Where can I get the best vacation package deals for Chester?
You'll find amazing Chester package deals with Travelocity. Select from as many as 400 partner airlines and 1,000,000 worldwide properties and turn those travel fantasies into reality.
Why should I book my Chester vacation package via Travelocity?
Because you'll never wander on your own if you book your vacation through us, and we offer round-the-clock customer support and top-notch service to boot. Add to that our Price Match Guarantee and a huge range of experiences and destinations to pick from. We're here to help you jet off on the vacation of a lifetime.
Will I save money on my Chester car rental if I book it with hotels and flights?
Combining your car, flight and hotel into a Chester vacation package is an excellent way to land the best deal. Plus, having your own rental car gives you the freedom to find your way to all those big-name sights you're eager to check out. Located 100 mi from Chester, Mall of America is one attraction that should be on your itinerary. Turn up the tunes and make a day trip of it.
Which airport is best for Chester?
Rochester Intl. Airport (RST) (30 mi away from the downtown area), La Crosse Municipal Airport (LSE) (60 mi away from central Chester) and Mason City Municipal Airport (MCW) (55 mi away from central Chester) are all great options for Chester.

Photos of local treasures

Browse Chester vacation photos for more inspiration