Chester Vacation Packages

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Chester Hotel Deals

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
The price is CA $130 per night from Jul 28 to Jul 29
CA $130
CA $144 total
Jul 28 - Jul 29
includes taxes & fees
8/10 Very Good! (401 reviews)
"The halls and rooms smelled like they'd been smoked in. The price was good, the owner was nice"

Reviewed on Jul. 21, 2025

Americas Best Value Inn & Suites Spring Valley
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
The price is CA $148 per night from Aug 10 to Aug 11
CA $148
CA $166 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (253 reviews)
"The whole place was very clean. Good selection for breakfast."

Reviewed on Jul. 25, 2025

AmericInn by Wyndham Osage
Western Inn & Suites

Western Inn & Suites

2 out of 5
1530 Main St,, Osage, IA
Fully refundableReserve now, pay when you stay
The price is CA $79 per night from Aug 27 to Aug 28
CA $79
CA $89 total
Aug 27 - Aug 28
includes taxes & fees
6.2/10 (29 reviews)
Decent room for a decent price.
"Quick check in which i like but not very friendly room was basic no frills but nice. Had a mini fridge and coffee maker. But alarm clock did not work and it’s not upgraded. I know it’s stupid but i forgot my charging square but most hotels have the lamps with usb ports. This one did not. It was quiet ..."

Reviewed on Jul. 24, 2025

Western Inn & Suites
See all 27 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.