Chester Vacations from $679

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites Rochester South Mayo Clinic

Country Inn & Suites Rochester South Mayo Clinic

3 out of 5
Price was $742, price is now $679 per person
$679
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rochester (RST)
8.4/10 Very Good! (1,001 reviews)
Room was very spacious-appreciated the division between bedroom and sitting area. Hot tub was nice, but could be cleaned.

Reviewed on Jan 13, 2026

The Berkman

The Berkman

3 out of 5
Folwell
Price was $908, price is now $770 per person
$770
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rochester (RST)
9.6/10 Exceptional! (363 reviews)
It was a bit tricky finding our area we could park in but it worked out.

Reviewed on Jan 1, 2026

Aspen Select

Aspen Select

3.5 out of 5
Kutzky Park
Price was $777, price is now $695 per person
$695
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rochester (RST)
8.4/10 Very Good! (1,003 reviews)
The Parking was easy and secure

Reviewed on Jan 11, 2026

Hotel Indigo Rochester – Mayo Clinic Area by IHG

Hotel Indigo Rochester – Mayo Clinic Area by IHG

3.5 out of 5
Downtown Rochester
Price was $757, price is now $683 per person
$683
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rochester (RST)
8.8/10 Excellent! (867 reviews)
Property was excellent.

Reviewed on Jan 12, 2026

Aspen Suites

Aspen Suites

3 out of 5
Price was $831, price is now $762 per person
$762
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Rochester (RST)
9/10 Wonderful! (677 reviews)
The staff was very friendly, room was very clean

Reviewed on Jan 10, 2026

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Chester Hotel Deals

AmericInn by Wyndham Osage

AmericInn by Wyndham Osage

2.5 out of 5
2212 Highway 218 Osage IA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $108 total per night from Feb 1 to Feb 2
$108 total
Feb 1 - Feb 2
Total with taxes and fees
9.4/10 Exceptional! (277 reviews)
Great location. Nice room. Clean with most all necessary technology. Good hot breakfast supplied. Could use addition of some USB ports. Also, outside concrete walk needs some work.

Reviewed on Jan 10, 2026

AmericInn by Wyndham Osage
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
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $71 total per night from Jan 19 to Jan 20
$71 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (485 reviews)
Nice place

Reviewed on Jan 10, 2026

Super 8 by Wyndham Cresco IA
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
$114 nightly
The price is $126 total per night from Jan 14 to Jan 15
$126 total
Jan 14 - Jan 15
Total with taxes and fees
9.2/10 Wonderful! (102 reviews)
Nice staff and extremely clean room, pool, etc.

Reviewed on Oct 28, 2025

Country Trails Inn & Suites
See all 25 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 $679 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.