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
The price is ₩106,806 per night from Sep 7 to Sep 8
₩106,806
₩150,390 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on Aug 11, 2025

Berkshire Mountain Lodge
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 ₩128,924 per night from Aug 26 to Aug 27
₩128,924
₩147,555 total
Aug 26 - Aug 27
includes taxes & fees
7/10 Good! (1,002 reviews)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags."

Reviewed on Aug 7, 2025

Quality Inn West Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
The price is ₩180,068 per night from Aug 13 to Aug 14
₩180,068
₩209,193 total
Aug 13 - Aug 14
includes taxes & fees
9.2/10 Wonderful! (2,230 reviews)
"Liked it so much, that I booked another stay"

Reviewed on Aug 6, 2025

D. Hotel Suites & Spa
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.

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 many days is enough for Chesterfield?
With a well-organized travel plan, you can easily visit the top Chesterfield sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your Chesterfield vacation for longer.
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.