Chesterfield Vacations

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Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

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 AED 410 per night from Apr 22 to Apr 23
AED 410
AED 451 total
includes taxes & fees
22 Apr - 23 Apr
8/10 Very Good! (811 reviews)
"Booked hotel 10 weeks before the stay specifically so I could use the pool and hot tub for my health condition. 4 days before arriving (1 day AFTER penalty free cancellation), I noticed they posted on their web site the pool & hot tub would be closed for the next 4 weeks (starting a few week before ..."

Reviewed on 29 March 2025

Hampton Inn Brattleboro
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 AED 400 per night from Apr 6 to Apr 7
AED 400
AED 440 total
includes taxes & fees
6 Apr - 7 Apr
6.8/10 (1,000 reviews)
"Very nice clean and convenient accommodations"

Reviewed on 30 March 2025

Colonial Motel And Spa
The Putney Inn
The Putney Inn
2.5 out of 5
57 Putney Landing Rd, Putney, VT
Fully refundableReserve now, pay when you stay
The price is AED 343 per night from Apr 6 to Apr 7
AED 343
AED 374 total
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (1,003 reviews)
"Very quiet. Clean and cozy room."

Reviewed on 30 March 2025

The Putney Inn
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 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.

Discover the most popular places to visit in Chesterfield