Deals on vacations and trips to Chester

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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
Price was $462, price is now $407 per person
$407
per person
Feb 27 - Mar 1
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Americas Best Value Inn Zumbrota

Americas Best Value Inn Zumbrota

2 out of 5
Price was $860, price is now $783 per person
$783
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Rochester (RST)
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
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 $595, price is now $545 per person
$545
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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.
The Berkman

The Berkman

3 out of 5
Folwell
Price was $568, price is now $524 per person
$524
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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.
AmericInn by Wyndham Rochester Near Mayo Clinic

AmericInn by Wyndham Rochester Near Mayo Clinic

3 out of 5
Price was $472, price is now $446 per person
$446
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Rochester (RST)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Enjoy the 24-hour gym and free perks like continental breakfast and free self parking.

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
$95 nightly
The price is $107 total per night
$107 total
Jan 4 - Jan 5, 2026
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
$68 nightly
The price is $76 total per night
$76 total
Jan 4 - Jan 5, 2026
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
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
Jan 19 - Jan 20, 2026
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.
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
$114 nightly
The price is $126 total per night
$126 total
Jan 1 - Jan 2, 2026
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
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
Dec 24 - Dec 25
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
$298 nightly
The price is $320 total per night
$320 total
Dec 24 - Dec 25
Total with taxes and fees
This farm stay features laundry facilities.
Pet friendly
Air conditioning
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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.

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 $407. 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.

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