Chesterfield Vacation Packages

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Your Chesterfield Vacation

Skip the stress of organizing your next big adventure with a Chesterfield vacation package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Your perfect Chesterfield vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style.

Chesterfield 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 CA $180 per night from Feb. 13 to Feb. 14
CA $180
CA $209 total
includes taxes & fees
Feb 13 - Feb 14
9.2/10 Wonderful! (2,361 reviews)
"Comfortable. Homey. Desk clerk was friendly and helpful"

Reviewed on Feb. 10, 2025

D. Hotel Suites & Spa
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Feb. 18 to Feb. 19
CA $121
CA $138 total
includes taxes & fees
Feb 18 - Feb 19
6.8/10 (1,000 reviews)
"Thank you so much !!"

Reviewed on Jan. 20, 2025

Red Roof Inn PLUS+ West Springfield
Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee Springfield
2.5 out of 5
440 Memorial Dr, Chicopee, MA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Feb. 23 to Feb. 24
CA $138
CA $157 total
includes taxes & fees
Feb 23 - Feb 24
8.8/10 Excellent! (1,005 reviews)
"N /a"

Reviewed on Feb. 9, 2025

Tru by Hilton Chicopee Springfield
See all 451 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

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.