Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Rochester – Mayo Clinic Area by IHG
Downtown Rochester
CA $1,063
per person
Nov 13 - Nov 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rochester (RST)
8.8/10 Excellent! (1,013 reviews)
Three different rooms - all had old noisy refrigerators. Unplugged from electrical outlet to get to sleep at night.
Breakfast is at market rates - not included.
Parking at public ramp located next door is also an extra $16 nightly.
Enjoyed free transportation to Mayo Clinic for medical appointments.
Didn't get to bar but seemed to have a nice happy hour.
Reviewed on Oct 9, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Country Trails Inn & Suites
809 U.S. 52 Preston MN
Fully refundableReserve now, pay when you stay
CA $180
CA $199 total
Oct 11 - Oct 12
includes taxes & fees
9.4/10 Exceptional! (157 reviews)
"The place was very clean and taken care of."
Reviewed on Oct 9, 2026
Americas Best Value Inn & Suites Spring Valley
745 N Broadway St Spring Valley MN
Fully refundableReserve now, pay when you stay
CA $127
CA $140 total
Oct 12 - Oct 13
includes taxes & fees
Super 8 by Wyndham Cresco IA
511 Second Ave SE, Hwy 9 & 5th Street Cresco IA
Fully refundableReserve now, pay when you stay
CA $102
CA $114 total
Nov 8 - Nov 9
includes taxes & fees
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.
Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from CA $1,063 on Expedia for your Chester getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
You're likely to find lower prices and greater availability in January, February and November. Explore our cheap Chester vacation packages and you could land some great off-season deals.
How many days is enough for Chester?
The ideal duration for your Chester vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you enough time to tick off all the leading sights and discover some hidden gems along the way.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Chester package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chester adventure off to a flying start.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights individually. Better still, you can tailor your Chester trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you're considering an impromptu Chester adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Chester?
- Choose when to travel: Check your schedule and get your bags packed. Your preferred time of year and the activities on offer will also help you decide when to escape to Chester.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Chester.
- Decide how long to go for: Now that you know more about Chester, you can figure out the right length of your vacation. Create a draft plan and allocate enough time to cover everything you want to see.
- Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Chester vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
