Chester Vacations from $507

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $555, price is now $507 per person
$507
per person
Mar 27 - Mar 29
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Rochester (RST)
8.4/10 Very Good! (1,001 reviews)
The evening shift attendant was extremely helpful. Rooms were nice and clean. Breakfast was delicous , Will stay at the hotel in the future.

Reviewed on Jan 8, 2026

Kahler Grand Hotel

Kahler Grand Hotel

3 out of 5
Downtown Rochester
Price was $596, price is now $559 per person
$559
per person
Mar 27 - Mar 29
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Rochester (RST)
8.2/10 Very Good! (1,746 reviews)
There was not a free breakfast, so be prepared. Otherwise a very clean property. The staff were very courteous and approachable!

Reviewed on Jan 9, 2026

Kahler Inn and Suites - Mayo Clinic Area

Kahler Inn and Suites - Mayo Clinic Area

3.5 out of 5
Downtown Rochester
Price was $596, price is now $559 per person
$559
per person
Mar 27 - Mar 29
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Rochester (RST)
8/10 Very Good! (1,495 reviews)
The staff was courteous and the room was a suite so it had a lot of nice area.

Reviewed on Jan 9, 2026

Hampton Inn Rochester-South

Hampton Inn Rochester-South

2.5 out of 5
Price was $542, price is now $512 per person
$512
per person
Mar 27 - Mar 29
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Rochester (RST)
9/10 Wonderful! (1,006 reviews)
Fast check in-spacious room

Reviewed on Jan 9, 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 $538, price is now $519 per person
$519
per person
Mar 27 - Mar 29
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Rochester (RST)
8.8/10 Excellent! (867 reviews)
Great stay as always!

Reviewed on Jan 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

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
$97 nightly
The price is $109 total per night from Feb 8 to Feb 9
$109 total
Feb 8 - Feb 9
Total with taxes and fees
9.4/10 Exceptional! (276 reviews)
Very friendly check-in. We felt welcomed.

Reviewed on Jan 4, 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 18 to Jan 19
$71 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (484 reviews)
Clean rooms and friendly desk ladys , helpful when checking in and out

Reviewed on Jan 1, 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 12 to Jan 13
$126 total
Jan 12 - Jan 13
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)

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals from $507 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.