Chesterfield Holidays

    deals illustration
    Better together
    Save up to €185 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chesterfield

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 €91 per night from 6 Jul to 7 Jul
€91
6 Jul - 7 Jul
includes taxes & fees
6.6/10 (1,002 reviews)
"We like the room. Nice and spacious. Er"

Reviewed on 2 Jul 2025

Colonial Motel And Spa
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2 out of 5
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
The price is €84 per night from 20 Jul to 21 Jul
€84
20 Jul - 21 Jul
includes taxes & fees
7/10 Good! (999 reviews)
"Very quiet."

Reviewed on 31 May 2025

Days Inn by Wyndham Keene NH
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is €123 per night from 7 Jul to 8 Jul
€123
7 Jul - 8 Jul
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Nice hotel"

Reviewed on 28 Jun 2025

Best Western Plus Keene Hotel
See all 513 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.

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.