Chester Vacations

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    Save up to SAR 390 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 SAR 456 per night from Apr 21 to Apr 22
SAR 456
SAR 530 total
includes taxes & fees
21 Apr - 22 Apr
9.2/10 Wonderful! (2,301 reviews)
"Great accommodations the pool was very nice and the staff was exceptional"

Reviewed on 16 April 2025

D. Hotel Suites & Spa
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is SAR 484 per night from Apr 20 to Apr 21
SAR 484
SAR 541 total
includes taxes & fees
20 Apr - 21 Apr
9/10 Wonderful! (557 reviews)
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on 14 April 2025

Life House Berkshires
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 SAR 316 per night from May 4 to May 5
SAR 316
SAR 361 total
includes taxes & fees
4 May - 5 May
7/10 Good! (1,000 reviews)
"It was ok"

Reviewed on 7 April 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.

Discover the most popular places to visit in Chester