Chesterfield Holidays
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Top Flight + Hotel Deals in Chesterfield
Price found within the past 48 hours. Click for updated prices.
Lark Hotels 907 Main
Central Square
€1,310
per person
27 Oct - 3 Nov
found 16 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (267 reviews)
Lovely accommodations a short walk to MIT. Safe neighborhood with plenty of bars, coffee shops and restaurants steps aways. Will return for my next stay in Cambridge.
Reviewed on 20 Sept 2026
Top hotels in Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
€97
1 Oct - 2 Oct
includes taxes & fees
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
€124
27 Sept - 28 Sept
includes taxes & fees
9.2/10 Wonderful! (2,072 reviews)
"Everything was awesome"
Reviewed on 19 Sept 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundable
€96
7 Oct - 8 Oct
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"I did love how free breakfast was, despite options for fruit were low. The pool was very clean and area around it very inviting despite the floor was slightly ramped."
Reviewed on 19 Sept 2026
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.
Stay near popular Chesterfield attractions
Chesterfield Gorge
Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.
Oak Hill
Commune with nature and explore the great outdoors at Oak Hill during your travels in Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Krug Sugarbush
You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Frequently asked questions
How much does a Chesterfield holiday package cost?
You'll find cheap prices from €655 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday 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 holiday packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organised 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 holiday 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 holiday as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalised holiday 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 holiday package to Chesterfield?
If you have your Chesterfield holiday 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?
- Pick your dates: The things you'd like to do in Chesterfield and your preferred season will help you decide when to get away.
- 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.
- 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.
- Combine your accommodation and airfare: After you've settled on your travel dates and duration, book the right Chesterfield holiday package for you.
Explore a world of travel with Expedia
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- Becket Land Trust Historic Quarry
- Visit Sherwood Forest
- Visit Becket
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- Visit Charlemont
- Charles H. Baldwin & Sons
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- Visit Lee
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- Studio 21 South
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- Visit Whately
- White Barn Studio
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
