Chesterfield Vacations from $327
Book a Hotel + Flight or Car together to unlock savings
Your Chesterfield Vacation
When a city escape is calling, answer it with a vacation package to Chesterfield. With all your travel arrangements in order before you go, all you need to do here is focus on having the time of your life. Fill your free time with tours of Spofford Lake, Asbury United Methodist Church and Madame Sherris Castle Ruins, some of the top attractions you really should see during your trip to Chesterfield. Whoever you're taking a break with and whatever the size of your budget, your ultimate Chesterfield vacation is just a few clicks away with Expedia.
The Latest Chesterfield vacation packages
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View all tripsStay near popular Chesterfield attractions
Asbury United Methodist Church
You can learn about the history of Chesterfield with a trip to Asbury United Methodist Church. Amble around the area's riverfront, or seek out its ski slopes.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Make some time to visit the shops while you're in the area.
Chesterfield Hotel Deals
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$99 nightly
$109 total
Nov 1 - Nov 2
Total with taxes and fees
6.2/10 (89 reviews)
"Lovely visit. Friendly staff."
Reviewed on Oct 12, 2026
Latchis Hotel
50 Main Street Brattleboro VT
$142 nightly
$156 total
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$142 nightly
$154 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Find the Best Chesterfield Vacation Packages
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Colonial Theatre, Pisgah State Park and Cheshire Childrens Museum |
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Frequently asked questions
What are the top things to do in Chesterfield?
Chesterfield, an outdoor and nature destination, offers a variety of scenic attractions and activities for your Chesterfield vacation:Browse and book things to do in Chesterfield on Expedia.
How can I save money on a Chesterfield vacation package?
When you bundle, you can save up to 30%*. To save money on a Chesterfield package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Do you need to rent a car in Chesterfield, or is public transport enough?
For a Chesterfield vacation package, renting a car is highly recommended to fully explore this outdoor and nature destination. Attractions like Spofford Lake and Chesterfield Gorge Natural Area are spread out, and a car offers the flexibility to visit them at your own pace. When arriving for your Chesterfield vacation packages with flights, you'll fly into airports such as Boston, MA (BOS-Logan Intl.), Hartford, CT (BDL-Bradley Intl.), Albany, NY (ALB-Albany Intl.), Manchester, NH (MHT-Manchester-Boston Regional), or Worcester, MA (ORH-Worcester Regional), all of which require onward transportation to Chesterfield. A rental car provides the most convenient way to get around and enjoy the scenic views.
Can I change or cancel my Chesterfield vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chesterfield vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chesterfield vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chesterfield?
To find last-minute vacation packages to Chesterfield, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chesterfield vacation packages?
Free cancellation on a Chesterfield vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chesterfield vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chesterfield getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chesterfield vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.