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.
Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

2 out of 5
Price was $610, price is now $588 per person
$588
per person
Nov 17 - Nov 20
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Express check-out and laundry facilities are also provided.
Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow

3 out of 5
Price was $796, price is now $738 per person
$738
per person
Nov 17 - Nov 20
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. Laundry facilities, barbecue grills, and a virtual front desk are also on offer.
Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

2.5 out of 5
Price was $752, price is now $733 per person
$733
per person
Nov 17 - Nov 20
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
This hotel features an indoor pool and a 24-hour gym. Bring the family and enjoy the children's pool, waterslide, and arcade/game room. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Fairfield Inn & Suites by Marriott Winona

Fairfield Inn & Suites by Marriott Winona

2.5 out of 5
Price was $772, price is now $766 per person
$766
per person
Nov 17 - Nov 20
found 23 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.

Top Chester hotels deals

Country Trails Inn & Suites

Country Trails Inn & Suites

2 out of 5
809 U.S. 52, Preston, MN
$126 nightly
The price is $140 total per night
$140 total
Oct 19 - Oct 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
$90 nightly
The price is $99 total per night
$99 total
Oct 19 - Oct 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.
Breakfast included
Pet friendly
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
$70 nightly
The price is $78 total per night
$78 total
Nov 2 - Nov 3
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
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
$99 nightly
The price is $110 total per night
$110 total
Oct 26 - Oct 27
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
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
Oct 16 - Oct 17
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
Country Lodge inn

Country Lodge inn

2 out of 5
525 Main Ave N, Harmony, MN
$143 nightly
The price is $158 total per night
$158 total
Oct 16 - Oct 17
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Parking included
Free WiFi
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 $588. 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