Chesterfield Vacations from $522
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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.
Attitash Mountain Village
$625
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
8.6/10 Excellent! (569 reviews)
Very nice condo. Must be very popular in the winter. Spacious room with a Murphy bed. Slept very good. Restaurant on side was not open but very friendly staff directed us to thing to see in the neighborhood and places to eat
Reviewed on Aug 20, 2026
The Inn at Thorn Hill & Spa
$1,437
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Manchester (MHT)
9.8/10 Exceptional! (1,004 reviews)
I’ve stayed at Thornhill several times. The experience is phenomenal from the beginning to end. The check-in process is wonderful. The rooms are all absolutely beautiful. The dinner is so good. I would drive there just for dinner if I didn’t have time to stay the night. Everybody is kind and everybody is eager to assist you with anything you need. I highly recommend.
Reviewed on Aug 25, 2026
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See all available trips from Singapore 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
$128 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Has everything necessary for a two night stay."
Reviewed on Aug 28, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$83 nightly
$91 total
Sep 7 - Sep 8
Total with taxes and fees
6.8/10 (46 reviews)
"It was dirty. The sink, bathroom, tub, floors. All dead bugs all over. TV was great. But a very musty smell in room. My sheets were not dry when we went to bed."
Reviewed on Aug 26, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$160 nightly
$175 total
Aug 30 - Aug 31
Total with taxes and fees
8.6/10 Excellent! (969 reviews)
"Great stay! Very clean."
Reviewed on Aug 28, 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 $522 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.
