Chester Vacations

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Find the Best Chester Vacation Packages

Chester Hotel Deals

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 AEDĀ 437 per night from Aug 11 to Aug 12
AEDĀ 437
AEDĀ 496 total
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (1,292 reviews)
"Very dirty, room hadn't been cleaned, nail clippings, old wrappers dirt on the floor. Very noisy, kids running in the hallways late at night banging on doors waking people up. The beds and sheets were clean. Breakfast was ok but tables were dirty and not cleaned between guests. Area around the hotel ..."

Reviewed on 21 July 2026

La Quinta Inn & Suites by Wyndham Springfield MA
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 694 per night from Jul 23 to Jul 24
AEDĀ 694
AEDĀ 775 total
23 Jul - 24 Jul
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"I get it. We get what we pay for and this is reasonably priced. The breakfast is okay. But the issue is that the sheets and comforter were stained. And then I opened up a towel and it wasnā€™t cleaned at all. Iā€™d gotten in late so I told the front desk when checking out the following morning. I was ..."

Reviewed on 22 July 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AEDĀ 460 per night from Aug 19 to Aug 20
AEDĀ 460
AEDĀ 596 total
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (1,018 reviews)
"Accommodations were excellent. Large living room,, well e"

Reviewed on 21 July 2026

Berkshire Mountain Lodge
See all 877 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.

Stay near popular Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.
See properties

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 ā€” ideal for a budget-friendly getaway.
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.
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 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.