Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Chester Holiday

Our pick of the best Chester Hotel Deals

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 NZ$249 per night from 12 July to 13 July
NZ$249
12 July - 13 July
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Vert clean, incluses breakfast so so"

Reviewed on 6 July 2026

The Yankee Inn
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
The price is NZ$200 per night from 4 Aug to 5 Aug
NZ$200
4 Aug - 5 Aug
includes taxes & fees
7/10 Good! (1,010 reviews)
"Breakfast was good a/c excellent actually cold. It was 90 outside the whole place nice and cool. Bed comfortable plenty of towels. The vending machines could use updating only cash or coins. There is gas station next door so you could get stuff there too."

Reviewed on 6 July 2026

Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is NZ$301 per night from 5 Aug to 6 Aug
NZ$301
5 Aug - 6 Aug
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"Nice property good coffee"

Reviewed on 6 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 on your trip to Chester. Wander the lakeside and forests in this relaxing area.
See properties

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.

Explore a world of travel with Expedia

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