Chester Holidays

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Photo by Elizabeth Massa Peroulakis

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Your Chester Holiday

The lively city of Chester is calling. Uncover both its hidden gems and highlights with a Chester holiday package that's tailored to you. Chester Town Hall and Becket Land Trust Historic Quarry are some of the major attractions to check out during a trip to Chester. No matter your travel plans or budget, putting together the ultimate tailored Chester holiday is a walk in the park with Expedia.

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
630
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Maple Corner Farm Cross Country Ski Area, Blandford Ski Area and Chester Town Hall

Our pick of the best 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
8.8/10 Excellent! (573 reviews)
I’d stay there again
"Everything was nice expect the “last guests” socks we found tangled in the pull out sofa bed."

Reviewed on 17 Aug. 2025

Get rates
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
The price is AU$202 per night from 27 Aug to 28 Aug
AU$202
27 Aug - 28 Aug
includes taxes & fees
8/10 Very Good! (1,272 reviews)
"Everyone was nice. It needs a little updating/painting"

Reviewed on 12 Aug. 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 AU$185 per night from 24 Aug to 25 Aug
AU$185
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (2,218 reviews)
"Lovely property. The front desk clerk was angry and bitter and the breakfast was underwhelming but otherwise, ok."

Reviewed on 13 Aug. 2025

D. Hotel Suites & Spa
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chester holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday 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 holiday package, consider planning a trip in January, February and November. You'll usually find lower rates on flights and accommodation during these months — ideal for a budget-friendly break.
How many days is enough for Chester?
The ideal duration for your Chester holiday 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chester holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging stays and flights individually. Better still, you can customise 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 holiday 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, favourite 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 accommodation 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 holiday package.

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