Chester Vacations from $370

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
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 $554, price is now $370 per person
$370
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rochester (RST)
8.8/10 Excellent! (867 reviews)
room clean poor location

Reviewed on Nov 24, 2025

Kahler Grand Hotel

Kahler Grand Hotel

3 out of 5
Downtown Rochester
Price was $702, price is now $519 per person
$519
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rochester (RST)
8.2/10 Very Good! (1,746 reviews)
Did know about a breakfast included in our room fee.

Reviewed on Dec 4, 2025

Centerstone Plaza Hotel Soldiers Field - Mayo Clinic Area

Centerstone Plaza Hotel Soldiers Field - Mayo Clinic Area

3 out of 5
Historic Southwest
Price was $656, price is now $540 per person
$540
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rochester (RST)
8.6/10 Excellent! (1,003 reviews)
The room was clean, the staff was very friendly and helpful.

Reviewed on Nov 29, 2025

Staybridge Suites Rochester - Mayo Clinic Area by IHG

Staybridge Suites Rochester - Mayo Clinic Area by IHG

3 out of 5
Kutzky Park
Price was $630, price is now $542 per person
$542
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rochester (RST)
9.4/10 Exceptional! (414 reviews)
Parking is a pain in the neck. Street parking and very limited underground parking.

Reviewed on Nov 24, 2025

EVEN Hotel Rochester - Mayo Clinic Area by IHG

EVEN Hotel Rochester - Mayo Clinic Area by IHG

4 out of 5
Kutzky Park
Price was $560, price is now $488 per person
$488
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rochester (RST)
9.4/10 Exceptional! (937 reviews)
Very nice guest services. Fast efficient check in. Nice room. One of the blinds was jammed and would not close all the way. Told front desk of the issue. Hopefully they get it fixed before the next guests. Pool and hot tub were nice. Great covered parking. Highly recommend.

Reviewed on Nov 27, 2025

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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
$91 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
9.4/10 Exceptional! (271 reviews)
Nice room. Clean. Quiet. Hot tub was hot. Pool was too cold. Good breakfast options.

Reviewed on Nov 14, 2025

AmericInn by Wyndham Osage
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
$89 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (432 reviews)
Very clean, spotless everywhere. Kind, friendly check-in. Happy Happy!

Reviewed on Nov 25, 2025

Americas Best Value Inn & Suites Spring Valley
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 1 to Jan 2
$126 total
Jan 1 - Jan 2, 2026
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 $370 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.