Chesterfield Vacations

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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.

Discover the most popular places to visit in Chesterfield

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.

Asbury United Methodist Church

Chesterfield Hotel Deals

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $86 total per night from Dec 17 to Dec 18
$86 total
Dec 17 - Dec 18
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
Room very nice, comfortable clean

Reviewed on Nov 29, 2025

The Covered Bridge Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $161 total per night from Dec 23 to Dec 24
$161 total
Dec 23 - Dec 24
Total with taxes and fees
8.2/10 Very Good! (925 reviews)
Convenient, clean. Staff was very friendly and helpful. Close to Highway. Keys weren’t working when we returned from a long day out. TV was also not working, but luckily we were in the room for only a short time before heading out for dinner.

Reviewed on Dec 8, 2025

Hampton Inn Brattleboro
The White House Inn

The White House Inn

3.5 out of 5
178 Route 9 East Wilmington VT
$184 nightly
The price is $202 total per night from Jan 4 to Jan 5
$202 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (262 reviews)
There was no hot water the first night.. I let the staff know the next day .. the young man immediately checked room availability and offered 3 options.. he also asked if he could help move us The room was clean. The fireplace was wonderful staff was friendly and accommodating

Reviewed on Dec 12, 2025

The White House Inn
See all 518 properties in Chesterfield
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 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.