Chesterfield Vacations from $750
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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.
Hideaway Inn Mt.Sunapee
$750
per person
Oct 23 - Oct 30
found 1 hour ago
Roundtrip flight included
Houston (IAH) to Manchester (MHT)
8.4/10 Very Good! (261 reviews)
This is a good basic place to stay- there isn't many frills. It provides a nice bed and bathroom. Good for a stay when you just need the essentials.
Location for Mt Sunapee is excellent.
Reviewed on Sep 1, 2026
The Village of Loon Mountain Fixed Rooms
$803
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Manchester (MHT)
8.6/10 Excellent! (65 reviews)
The location is the best and everything was easy to get to. It was quiet, clean and refreshing. Only minutes from anything you need.
The only thing was the bed was very uncomfortable you could feel the springs in the mattress. Other than that it was perfect
Reviewed on Sep 2, 2026
Kearsarge Inn
North Conway Village
$896
per person
Oct 15 - Oct 20
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Manchester (MHT)
9.8/10 Exceptional! (1,004 reviews)
We spent 3 night and lived the location. Quick walk to town for shopping and restaurants. Free parking. The inn is very quiet. Comfortable bed, great shower. We were in room 6. Very basic but that’s exactly what we were looking for.
Reviewed on Sep 7, 2026
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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
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$102 nightly
$112 total
Sep 9 - Sep 10
Total with taxes and fees
8.6/10 Excellent! (976 reviews)
"Considering the age of the property, this is a great stay! The staff was super helpful upon arrival, helping with check-in, parking and directions. The proximity to shops and restaurants is amazing. The room was clean and comfortable. I love that there were extra fans in the room to account for the ..."
Reviewed on Sep 5, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$83 nightly
$91 total
Sep 9 - Sep 10
Total with taxes and fees
6.6/10 (54 reviews)
"The room was dirty and smelled musty and of urine. The hallways have all broken down ice machines and the breakfast was non-existent."
Reviewed on Sep 6, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
$149 nightly
$162 total
Sep 13 - Sep 14
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
How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $750 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.
