Chester Holidays

Photo by Elizabeth Massa Peroulakis

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chester

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,267 reviews)
"I loved this hotel. They had a pool and whirlpool, which is awesome! Breakfast was really good. One day they had French toast, chicken sausage, eggs, potatoes and cold items. The staff are friendly. Room was very clean, just not super updated. They also have a coin-operated washer and dryer. Great ..."

Reviewed on 5 Jun, 2025

Get rates
D. Hotel Suites & Spa
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 S$124 per night from 29 Jun to 30 Jun
S$124
29 Jun - 30 Jun
includes taxes & fees
7/10 Good! (1,007 reviews)
"The pool is outdoors but in an extended tent. You get what you paid for."

Reviewed on 9 Jun, 2025

Quality Inn West Springfield
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
Fully refundableReserve now, pay when you stay
The price is S$214 per night from 17 Jun to 18 Jun
S$214
17 Jun - 18 Jun
includes taxes & fees
9/10 Wonderful! (705 reviews)
"I can highly recommend The Ellery. Lovely place to stay. Convenient. Excellent continental breakfast."

Reviewed on 8 Jun, 2025

The Ellery
See all 829 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.