Chesterfield Vacations

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Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (571 reviews)
"Shower/tub side in accessible room was extremely high fyi."

Reviewed on 17 August 2025

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Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
The price is AED 380 per night from Aug 24 to Aug 25
AED 380
AED 441 total
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (2,226 reviews)
"I enjoyed my stay"

Reviewed on 18 August 2025

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 AED 325 per night from Sep 7 to Sep 8
AED 325
AED 371 total
7 Sep - 8 Sep
includes taxes & fees
7/10 Good! (1,001 reviews)
Enjoyable one night stay at the Quality Inn!
"I recently stayed 1 night at the Quality Inn while in the area for Six Flags. This is my go to hotel when visiting the park as it is a great value and about 15 minutes away. I checked in later, around 9pm, and long time employee Rick was at the desk. He is never shy about his dislike for computers ..."

Reviewed on 12 August 2025

Quality Inn West Springfield
See all 466 properties in Chesterfield
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.

Discover the most popular places to visit in Chesterfield

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.

Chesterfield Gorge

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You can usually find reduced prices and greater availability in January, February and November. Browse our cheap Chesterfield vacation packages and you could get some excellent off-season deals.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesterfield?
If you have your Chesterfield vacation dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
  2. Budget wisely: Besides the cost of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Chesterfield.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to experience in Chesterfield. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the right Chesterfield vacation package for you.