Chester Vacation Packages

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Photo by Elizabeth Massa Peroulakis

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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.

Ready to book your vacation to Chester?

 

Choose your dates

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 CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (578 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."

Reviewed on Aug. 18, 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
The price is CA $160 per night from Aug 27 to Aug 28
CA $160
CA $181 total
Aug 27 - Aug 28
includes taxes & fees
8/10 Very Good! (1,278 reviews)
"Na"

Reviewed on Aug. 18, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
The price is CA $143 per night from Aug 24 to Aug 25
CA $143
CA $166 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (2,224 reviews)
"The gentleman at the front desk was amazing. I don’t usually leave reviews but he was possibly the most professional individual that I have met. He made us feel welcome, informed, and comfortable. The hotel exceeded expectations and had everything the tired road travel or couple on a getaway could ..."

Reviewed on Aug. 18, 2025

D. Hotel Suites & Spa
See all 835 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, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
If you're hoping to score a cheap Chester vacation package, consider planning a trip in January, February and November. You'll typically find lower rates on flights and accommodations during these months — ideal for a budget-friendly getaway.
How many days is enough for Chester?
With a well-organized itinerary, you can easily hit the top Chester sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Chester vacation for longer.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor 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 right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
How to plan a trip to Chester?

  1. Choose when to get away: Check your diary and get packing. Your preferred season and the available activities will also help you decide when to escape to Chester.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Chester.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Chester. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Chester vacation package.

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