Chester Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Elizabeth Massa Peroulakis

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

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

    Rest easy

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

Your Chester Vacation

Our vacation packages to Chester allow you to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this fantastic city. There's a whole load to see during a trip to Chester, including Becket Land Trust Historic Quarry and Chester Town Hall. Check out Expedia's wide range of travel options and book your ultimate vacation to Chester today.

Chester Hotel Deals

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $106 total per night from Aug 18 to Aug 19
$106 total
Aug 18 - Aug 19
Total includes taxes and fees
7/10 Good! (1,000 reviews)
"Staff was very friendly. The price was right"

Reviewed on Aug 4, 2025

Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $145 total per night from Sep 7 to Sep 8
$145 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on Aug 5, 2025

Berkshire Mountain Lodge
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Aug 21 to Aug 22
$129 total
Aug 21 - Aug 22
Total includes taxes and fees
8/10 Very Good! (1,276 reviews)
"Place is clean"

Reviewed on Aug 2, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
See all 833 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.

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?
You can snap up a vacation package to this top destination on Expedia. But how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chester?
November, December and January are the best times to search for cheap Chester vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Chester?
The ideal length of your Chester vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to hit all the leading sights and discover some hidden spots along the way.
How to find the best Chester package deals?
Landing a cheap Chester package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" 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 often lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can customize your Chester escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chester?
If you have your Chester travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Set off on your dream getaway to Chester with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.