Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Chesterfield Holiday

Our Chesterfield holiday packages allow you to customise your own adventure. Tailor your journey to your interests and needs and make the most of your time in this interesting city. Fill up your itinerary with tours of Spofford Lake, Madame Sherri Forest and Asbury United Methodist Church, some of the top attractions you just have to see during a trip to Chesterfield. A couple of quick clicks is all it takes to craft your perfect Chesterfield holiday on Expedia.

Chesterfield Holiday

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
3,800
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Colonial Theatre, Historical Society of Cheshire County and Pisgah State Park

Our pick of the best Chesterfield Hotel Deals

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$236 per night from 11 Aug to 12 Aug
AU$236
11 Aug - 12 Aug
includes taxes & fees
6.6/10 (1,002 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on 28 Jul. 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$205 per night from 4 Sept to 5 Sept
AU$205
4 Sept - 5 Sept
includes taxes & fees
8/10 Very Good! (862 reviews)
"Didn’t like the fact that I was suppose to be charge when I checked in but they charged my card before I arrived."

Reviewed on 9 Aug. 2025

Hampton Inn Brattleboro
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 17 Aug to 18 Aug
AU$208
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (873 reviews)
"Staff were friendly, room clean and comfortable"

Reviewed on 7 Aug. 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 504 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chesterfield holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday 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're looking to snag a cheap Chesterfield holiday package, consider planning a trip in January, February and March. You'll generally find better rates on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chesterfield?
Usually, a handful of days is enough to go to the top sights during your Chesterfield holiday. But if you want to have more time to rest or take day trips, consider extending your itinerary.
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 holiday package as soon as possible.
Is it cheaper to book a Chesterfield holiday as a package?
Expedia holiday 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 personalised Chesterfield holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you plan to do in Chesterfield and your favourite season will help you decide when to go.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to save for your trip to Chesterfield. Then, pick a property that matches your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Work out your trip length: Consider how long you'd like to spend exploring Chesterfield. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Chesterfield holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.