Chesterfield Vacations from $348
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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
Price found within the past 48 hours. Click for updated prices.
Eastern Slope Inn Resort
North Conway Village
$348
per person
Sep 13 - Sep 15
found 18 hours ago
Roundtrip flight included
New York (NYC) to Manchester (MHT)
8.8/10 Excellent! (474 reviews)
Been going to the ESI for 40 years. Lots of shopping and food options. Kids liked the arcade. Plan on returning soon.
Reviewed on Aug 6, 2026
The Village of Loon Mountain Fixed Rooms
$1,221
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (59 reviews)
There was not adequate parking. The indoor and outdoor pools were freezing with the exception of one, but that one was loaded with children.
The paint was peeling everywhere. There were much needed repairs visible in the room, as well as in the pool area. The hotel only allowed one pool towel. The room had a fireplace that did not work and a toaster that also did not work.
We would never recommend this place.
Reviewed on Jul 22, 2026
Holiday Inn Express Hotel & Suites White River Junction by IHG
$873
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (1,001 reviews)
All around a great place…friendly staff, clean, good breakfast, easy access to two highways. Highly recommend for families since there are rooms for more than 4 people.
Reviewed on Aug 9, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
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
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$115 nightly
$125 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"As always, this place never disappoints. From the friendly staff that greets you at check-in, to the breakfast buffet that gives you a good variety to start your day… this will always be my go-to when visiting Keene."
Reviewed on Aug 8, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 19 - Aug 20
Total with taxes and fees
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$82 nightly
$89 total
Sep 1 - Sep 2
Total with taxes and fees
7/10 Good! (1,005 reviews)
"Found front desk noisy in everything after 9m and not available at check out time at 11 am"
Reviewed on Aug 11, 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.
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
How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $348 on Expedia. However, how much your vacation to Chesterfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Chesterfield?
If you'd like to snag a cheap Chesterfield vacation package, consider visiting in October, November and December. You'll typically find lower prices on flights and accommodations during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chesterfield?
With a well-planned schedule, you can easily hit the main Chesterfield sights in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some terrific Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Chesterfield package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Chesterfield vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield trip should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
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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.
