Chester Vacations from $400

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
America's Stay Inn Stewartville

America's Stay Inn Stewartville

2.5 out of 5
Price was $433, price is now $400 per person
$400
per person
Jun 25 - Jun 28
just found
Roundtrip flight included
Los Angeles (LAX) to Rochester (RST)
8/10 Very Good! (441 reviews)
Good location. Easy parking. Breakfast disappointing

Reviewed on May 13, 2026

The Towers At Kahler Grand Hotel

The Towers At Kahler Grand Hotel

4 out of 5
Downtown Rochester
Price was $881, price is now $794 per person
$794
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Memphis (MEM) to Rochester (RST)
9.4/10 Exceptional! (101 reviews)
What a wonderful and extremely helpful staff. So kind and helpful and accommodating. I will most definitely stay again. Such a wonderful experience!

Reviewed on May 23, 2026

Aspen Select

Aspen Select

3.5 out of 5
Kutzky Park
Price was $526, price is now $478 per person
$478
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Memphis (MEM) to Rochester (RST)
8.4/10 Very Good! (1,002 reviews)
Clean room and bathroom. Perfect climate control in room. Great on-site free parking. Simple good free breakfast. Nice place to relax and refresh. Very close to a great restaurant. Breakfast, lunch, and dinner or a cocktail.

Reviewed on May 20, 2026

La Quinta Inn & Suites by Wyndham Rochester Mayo Clinic S

La Quinta Inn & Suites by Wyndham Rochester Mayo Clinic S

3 out of 5
Price was $475, price is now $432 per person
$432
per person
Jun 25 - Jun 28
just found
Roundtrip flight included
Los Angeles (LAX) to Rochester (RST)
7.4/10 Good! (1,066 reviews)
Check in was straight forward. Staff was helpful. Room clean as well as the refrigerator, microwave and coffee maker. Breakfast was what you'd expect and was fine.

Reviewed on May 24, 2026

Super 8 by Wyndham Rochester Mayo Clinic Area

Super 8 by Wyndham Rochester Mayo Clinic Area

2 out of 5
Price was $444, price is now $411 per person
$411
per person
Jun 25 - Jun 28
just found
Roundtrip flight included
Los Angeles (LAX) to Rochester (RST)
7.8/10 Good! (1,006 reviews)
Room was minimal. Could have used some furniture. Desk clerk at checkout was extremely rude to another customer. Breakfast was fine. Ok.

Reviewed on May 11, 2026

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Chester Hotel Deals

Country Trails Inn & Suites

Country Trails Inn & Suites

2 out of 5
809 U.S. 52 Preston MN
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $140 total per night from May 26 to May 27
$140 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (116 reviews)
"Very clean"

Reviewed on May 24, 2026

Country Trails Inn & Suites
Western Inn & Suites

Western Inn & Suites

2 out of 5
1530 Main St, Osage IA
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $63 total per night from Jun 17 to Jun 18
$63 total
Jun 17 - Jun 18
Total with taxes and fees
6.2/10 (64 reviews)
"Rear Door of hotel. did not open. have double doors in front one not useable"

Reviewed on May 10, 2026

Western Inn & Suites
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
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $87 total per night from May 26 to May 27
$87 total
May 26 - May 27
Total with taxes and fees
8.2/10 Very Good! (446 reviews)
"Overall, the room was clean which I very much appreciate. However, I don't think they bleach the linens or towels. There were visible stains on them and they looked dingy. Breakfast was the bare minimum. A good place for a brief stay where your main goal is a bed and a shower. I have stayed here ..."

Reviewed on May 17, 2026

Americas Best Value Inn & Suites Spring Valley
See all 26 properties in Chester
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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rochester Intl. Airport (RST)

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Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals from $400 on Expedia, you'll be pleasantly surprised at how much a vacation to Chester costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chester?
You can typically find lower prices and better availability in February, April and September. Check out our cheap Chester vacation packages and you could get some great off-season deals.
How many days is enough for Chester?
Generally, a handful of days is enough to visit the top sights during your Chester vacation. But if you want to have some time to kick back or take day tours, consider extending your itinerary.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Chester package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chester?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester break.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Chester break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.