Chesterfield Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Chesterfield Vacation Packages

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 ₩133,237 per night from Jun 29 to Jun 30
₩133,237
₩146,561 total
Jun 29 - Jun 30
includes taxes & fees
6.8/10 (1,009 reviews)
"Setup is different. Pool, dining and Spa not connected to hotel. Its like a neighborhood instead. Rooms clean. Women in front office are all extremely nice. Would definitely go back."

Reviewed on Jun 22, 2025

Colonial Motel And Spa
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 ₩181,996 per night from Jun 29 to Jun 30
₩181,996
₩197,466 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Great breakfast selections"

Reviewed on Jun 24, 2025

Best Western Plus Keene Hotel
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ₩175,232 per night from Jul 6 to Jul 7
₩175,232
₩192,755 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (644 reviews)
"Buffer not always filled up Not always someone to the front desk 7: 10"

Reviewed on Jun 20, 2025

Comfort Inn & Suites Brattleboro I-91
See all 510 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.