Chester Vacation Packages

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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.

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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
The price is CA $121 per night from Jul 13 to Jul 14
CA $121
CA $139 total
Jul 13 - Jul 14
includes taxes & fees
7/10 Good! (1,005 reviews)
Clean Room, great value, and comfortable!
"Recently stayed two nights at the Quality Inn at the end of June. Check in was quick, staff was friendly, and I got my room request, towards the back of the building on a higher floor. I had room 423, it was clean, fairly good condition, everything worked, although fridge took a few hours to cool ..."

Reviewed on Jul. 2, 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 CA $155 per night from Jul 6 to Jul 7
CA $155
CA $176 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very Good! (1,279 reviews)
"Staff was all super friendly and helpful. Location was where I needed it to be. Renovation was going on, which meant I had to go up 2 floors on the elevator to find a working ice machine. Pool is not as attractive in person as it is in the photo."

Reviewed on Jun. 30, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 10 to Jul 11
CA $127
CA $146 total
Jul 10 - Jul 11
includes taxes & fees
6.8/10 (1,004 reviews)
"Rooms were clean and the staff was nice."

Reviewed on Jun. 29, 2025

Red Roof Inn PLUS+ West Springfield
See all 825 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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.