Chester Vacations

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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 475 per night from May 1 to May 2
AED 475
AED 552 total
includes taxes & fees
1 May - 2 May
9.2/10 Wonderful! (2,292 reviews)
"Consistently excellent stay- highly recommended Caring and professional staff Super clean rooms each with its own character Great free breakfast Great value !"

Reviewed on 23 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 AED 392 per night from May 7 to May 8
AED 392
AED 438 total
includes taxes & fees
7 May - 8 May
9/10 Wonderful! (565 reviews)
"It was an older motel, remodeled recently. It was a mini-vacation, a great place and great food."

Reviewed on 20 April 2025

Life House Berkshires
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 406 per night from Apr 27 to Apr 28
AED 406
AED 460 total
includes taxes & fees
27 Apr - 28 Apr
8/10 Very Good! (1,277 reviews)
"I like the views on the city because i was in 6th floor"

Reviewed on 22 April 2025

La Quinta Inn & Suites by Wyndham Springfield MA
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