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.
Days Inn by Wyndham Austin

Days Inn by Wyndham Austin

2 out of 5
Price was $453, price is now $407 per person
$407
per person
Oct 3 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rochester (RST)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Staff at the 24-hour front desk can provide around-the-clock assistance.
Aspen Select

Aspen Select

3.5 out of 5
Price was $534, price is now $441 per person
$441
per person
Oct 3 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
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 $518, price is now $455 per person
$455
per person
Oct 3 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Broadway Plaza, Trademark Collection by Wyndham

Broadway Plaza, Trademark Collection by Wyndham

3 out of 5
Downtown Rochester
Price was $727, price is now $643 per person
$643
per person
Oct 3 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rochester (RST)
This apartment features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a sauna on site, and a 24-hour front desk and dry cleaning are also provided.
Comfort Inn & Suites West - Medical Center

Comfort Inn & Suites West - Medical Center

3 out of 5
Price was $531, price is now $475 per person
$475
per person
Oct 3 - Oct 7
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rochester (RST)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Top Chester hotels deals

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
$95 nightly
The price is $105 total per night
$105 total
Aug 25 - Aug 26
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
$61 nightly
The price is $69 total per night
$69 total
Sep 24 - Sep 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.
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
Aug 25 - Aug 26
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.
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
Sep 21 - Sep 22
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.
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
Aug 25 - Aug 26
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
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
Sep 21 - Sep 22
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.
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 $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.

Photos of local treasures

Browse Chester vacation photos for more inspiration