Chester Vacations

Book a Hotel + Flight together to unlock savings

Photo by Elizabeth Massa Peroulakis
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    Save up to AED 148 when you book a flight and hotel together*
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Find the Best Chester Vacation Packages

Chester Hotel Deals

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundable
The price is AED 438 per night from Jun 8 to Jun 9
AED 438
AED 509 total
includes taxes & fees
8 Jun - 9 Jun
9.2/10 Wonderful! (2,277 reviews)
"Great room. Bed was very comfortable and the shower water pressure was fabulous!"

Reviewed on 26 May 2025

D. Hotel Suites & Spa
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 AED 418 per night from Jun 15 to Jun 16
AED 418
AED 475 total
includes taxes & fees
15 Jun - 16 Jun
8/10 Very Good! (1,275 reviews)
"Easy parking, room was nice."

Reviewed on 23 May 2025

La Quinta Inn & Suites by Wyndham Springfield MA
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 AED 309 per night from Jun 22 to Jun 23
AED 309
AED 354 total
includes taxes & fees
22 Jun - 23 Jun
7/10 Good! (1,000 reviews)
"The pool was closed. One of the main reasons why I chose the resort was the pool. Everything else was fine."

Reviewed on 27 May 2025

Quality Inn West Springfield
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 vacation package cost?
You can snap up a vacation package to this top destination on Expedia. But how much your vacation 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 vacation package, consider planning a trip in January, February and November. You’ll usually find lower rates on flights and accommodations during these months — ideal for a budget-friendly break.
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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can customize 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 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 the perfect time to travel: Your schedule, favorite 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 accommodations 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 vacation package.

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