Chesterfield Trips (flight + hotel)

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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 P5,519 per night from Jul 6 to Jul 7
P5,519
P6,070 total
Jul 6 - Jul 7
includes taxes & fees
6.6/10 (1,002 reviews)
"We like the room. Nice and spacious. Er"

Reviewed on Jul 2, 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 P5,116 per night from Jul 20 to Jul 21
P5,116
P5,551 total
Jul 20 - Jul 21
includes taxes & fees
7/10 Good! (1,000 reviews)
"Availability and close to different places to eat and visit."

Reviewed on Jul 4, 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 P7,538 per night from Jul 6 to Jul 7
P7,538
P8,179 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Nice hotel"

Reviewed on Jun 28, 2025

Best Western Plus Keene Hotel
See all 512 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 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're looking to snag a cheap Chesterfield vacation 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 vacation. 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 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.
How to plan a trip to Chesterfield?

  1. Pick your dates: The things you plan to do in Chesterfield and your favorite 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 personalized Chesterfield vacation package.

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