Chester Vacations from $861

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Great Northern Inn

Best Western Plus Great Northern Inn

2.5 out of 5
Price was $879, price is now $861 per person
$861
per person
Nov 28 - Nov 30
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Havre (HVR)
8.8/10 Excellent! (667 reviews)
Clean, comfortable bed and pillows

Reviewed on Sep 5, 2025

AmericInn by Wyndham Havre

AmericInn by Wyndham Havre

2.5 out of 5
Price was $887, price is now $867 per person
$867
per person
Nov 28 - Nov 30
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Havre (HVR)
9.2/10 Wonderful! (621 reviews)
Great place and service.

Reviewed on Sep 24, 2025

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Chester Hotel Deals

Great northern bed and breakfast

Great northern bed and breakfast

Chester
$214 nightly
The price is $231 total per night from Sep 29 to Sep 30
$231 total
Sep 29 - Sep 30
Total with taxes and fees
From Wold creek, MT
"Great"

Reviewed on Oct 2, 2024

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

The Westland Suite - Historic Lodging, Contemporary Comforts

Chester
$214 nightly
The price is $231 total per night from Sep 29 to Sep 30
$231 total
Sep 29 - Sep 30
Total with taxes and fees
10/10 Exceptional! (14 reviews)
Westland Suite
"Westland Suite was charming and fit our needs perfectly. Four adults and two teenagers stayed and all were very comfortable."

Reviewed on Jun 30, 2025

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

The Homestead - 3 bedroom House in the Heart of Chester

Chester
$214 nightly
The price is $231 total per night from Sep 29 to Sep 30
$231 total
Sep 29 - Sep 30
Total with taxes and fees
10/10 Exceptional! (23 reviews)
Peaceful and well provisioned
"We enjoyed our stay so much! Patty was an excellent host, and the property was sparkling clean and well provisioned! Would stau again."

Reviewed on May 26, 2025

The Homestead - 3 bedroom House in the Heart of Chester
See all 5 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.

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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 from $861 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.