Chester Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Elizabeth Massa Peroulakis

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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

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

Find the Best Chester Vacation Packages

Chester Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is ₩106,806 per night from Sep 7 to Sep 8
₩106,806
₩150,390 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on Aug 11, 2025

Berkshire Mountain Lodge
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
The price is ₩128,924 per night from Aug 26 to Aug 27
₩128,924
₩147,555 total
Aug 26 - Aug 27
includes taxes & fees
7/10 Good! (1,002 reviews)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags."

Reviewed on Aug 7, 2025

Quality Inn West Springfield
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
The price is ₩159,677 per night from Aug 21 to Aug 22
₩159,677
₩181,154 total
Aug 21 - Aug 22
includes taxes & fees
8/10 Very Good! (1,274 reviews)
"N/A"

Reviewed on Aug 8, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
See all 836 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.

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?
If you're looking to score a cheap Chester vacation package, consider planning a trip in January, February and November. You'll usually find lower rates on flights and accommodations during these months — ideal for a budget-friendly break.
How many days is enough for Chester?
The ideal duration for your Chester vacation depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to visit all the major sights and discover some hidden treasures 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.
How to plan a trip to Chester?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Chester.
  2. Work out your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Chester.
  3. Decide how long to go for: Now that you're more familiar with Chester, you can figure out the right length of your break. Create a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Chester vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.