Deals on vacations and trips to Chesterfield

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Chesterfield flight + hotel vacation packages

The Boston Hotel
Fairmont Copley Plaza, Boston
Boston Harbor Hotel
The Langham, Boston
Encore Boston Harbor
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Top Chesterfield hotels deals

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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.

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Frequently asked questions

How much are vacation packages to Chesterfield?
Travelocity offers hotel and flight packages from an incredible $599. With these kinds of deals, you’ll be exploring all of Chesterfield before too long.
Where can I get the best vacation package deals for Chesterfield?
You’ll find a fantastic range of Chesterfield package deals on Travelocity. With no less than 400 airlines and 1,000,000 worldwide properties, arranging the perfect vacation won’t take long.
Why should I purchase my Chesterfield vacation package with Travelocity?
Whether you’re searching for the ultimate unplugged getaway or you crave the fun and excitement of the big city, booking everything with Travelocity saves you time, hassle and money. No need to scour through countless websites looking for the best deal — our Price Match Guarantee ensures you’ll always get the lowest possible price, and our team of customer service experts are available 24/7 should you need them.
Can I save on my Chesterfield car rental if I bundle it with a hotel or flight?
Certainly — combine your car, hotel and flight into a Chesterfield vacation package and you can save a ton. With so much to see and do in and around Chesterfield, having your own set of wheels will make exploring a joy. Once you’re in the driver’s seat, crank up the music and cruise toward Fenway Park, a top attraction around 90 mi from Chesterfield.
What is the best time of year to go to Chesterfield?
Vacationing in the least busy months, November, December and January, comes with advantages — think cheaper flights and hotels and less bumping shoulders with tourist hordes. But there’s magic in the destination in the peak season. More events will be staged and more attractions will be open in June, July and August. If you’re watching your budget, generally offers the cheapest hotel prices. You’ll pay more for a room in .
Which airport is best for Chesterfield?
Bradley Intl. Airport (BDL), located around 35 mi south of downtown Chesterfield, is most likely where you’ll jet into. Your other choices are Albany Intl. Airport (ALB) (55 mi away from central Chesterfield) and Hartford, CT (HFD-Hartford - Brainard) (45 mi away from central Chesterfield).
What is there to do in Chesterfield?
Chesterfield Gorge is one of the awesome sights that make Chesterfield such a popular tourist destination. But give yourself enough time to experience its lesser-known attractions too. This is often where the best vacation memories are created.
Where should I stay when visiting Chesterfield?
If you’re after a place to spend your nights, have a look at the Elegant Wilderness Cabin 12 Miles From Northampton. It’s the top pick for many travelers.