Chester Vacations

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Chester Hotel Deals

The Homestead - 3 bedroom House in the Heart of Chester

The Homestead - 3 bedroom House in the Heart of Chester

Chester MT
$222 nightly
The price is $240 total per night from May 21 to May 22
$240 total
May 21 - May 22
Total with taxes and fees
10/10 Exceptional! (24 reviews)
"Perfect, quiet space that housed my brothers and I comfortably. Couldn’t have asked for better in a small town accommodation!"

Reviewed on Jan 6, 2026

The Homestead - 3 bedroom House in the Heart of Chester
The Westland Suite - Historic Lodging, Contemporary Comforts

The Westland Suite - Historic Lodging, Contemporary Comforts

Chester MT
$222 nightly
The price is $240 total per night from May 21 to May 22
$240 total
May 21 - May 22
Total with taxes and fees
9.8/10 Exceptional! (16 reviews)
"The host was great. The place was nice and clean."

Reviewed on Feb 5, 2026

The Westland Suite - Historic Lodging, Contemporary Comforts
Great northern bed and breakfast

Great northern bed and breakfast

Chester MT
$222 nightly
The price is $240 total per night from May 21 to May 22
$240 total
May 21 - May 22
Total with taxes and fees
9.8/10 Exceptional! (9 reviews)
From Wold creek, MT
"Great"

Reviewed on Oct 2, 2024

Great northern bed and breakfast
See all 4 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
Population
880

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Frequently asked questions

How much does a Chester vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, how much your vacation to Chester costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chester?
You can generally find lower prices and better availability in June, November and December. Explore our cheap Chester vacation packages and you could get some great off-season deals.
How many days is enough for Chester?
The ideal duration of your Chester vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to visit all the main sights and discover some hidden treasures along the way.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Chester package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chester getaway off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you're considering a spontaneous Chester trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're anything 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've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Chester trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.