Chester Vacations from $506

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Rochester-South

Hampton Inn Rochester-South

2.5 out of 5
Price was $643, price is now $506 per person
$506
per person
Dec 14 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rochester (RST)
9/10 Wonderful! (1,023 reviews)
Room was small but clean, continental breakfast was good as usual.

Reviewed on Nov 9, 2025

Aspen Select

Aspen Select

3.5 out of 5
Price was $766, price is now $544 per person
$544
per person
Dec 14 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rochester (RST)
8.4/10 Very Good! (1,005 reviews)
Safe parking very clean and breakfast had options for anyone

Reviewed on Nov 7, 2025

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 $685, price is now $527 per person
$527
per person
Dec 14 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rochester (RST)
8.8/10 Excellent! (837 reviews)
Beautiful room, spotless

Reviewed on Nov 9, 2025

The Towers At Kahler Grand Hotel

The Towers At Kahler Grand Hotel

4 out of 5
Downtown Rochester
Save 100% on your flight
Price was $1,843, price is now $1,426 per person
$1,426
per person
Dec 14 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rochester (RST)
9.4/10 Exceptional! (88 reviews)
Concierge was amazing! Breakfast and amazing dinner included with stay. Literally across the street from Mayo and Ruth Chris on the first level.

Reviewed on Oct 4, 2025

The Berkman

The Berkman

3 out of 5
Folwell
Price was $1,097, price is now $882 per person
$882
per person
Dec 14 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rochester (RST)
9.6/10 Exceptional! (352 reviews)
Beautiful, spacious room with excellent amenities. Hotel had fantastic gym, store, and lounge areas. Loved having Red Cow in the building. Across the street from St. Mary’s Hospital. Extremely courteous staff offered our family flexibility as we navigated our Mayo visit. Would absolutely stay again. Thank you for your excellent hospitality…

Reviewed on Nov 9, 2025

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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 Nov 11 to Nov 12
$140 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (103 reviews)
Nice staff and extremely clean room, pool, etc.

Reviewed on Oct 28, 2025

Country Trails 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
$85 nightly
The price is $94 total per night from Nov 16 to Nov 17
$94 total
Nov 16 - Nov 17
Total with taxes and fees
8/10 Very Good! (429 reviews)
Wonderful king suite. Friendly staff.

Reviewed on Oct 31, 2025

Americas Best Value Inn & Suites Spring Valley
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
$69 nightly
The price is $77 total per night from Nov 17 to Nov 18
$77 total
Nov 17 - Nov 18
Total with taxes and fees
8.4/10 Very Good! (474 reviews)
Good weekend breakfast

Reviewed on Oct 18, 2025

Super 8 by Wyndham Cresco IA
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 $506 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.