Chesterfield Vacations from $403

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Your Chesterfield Vacation

When a city escape is calling, answer it with a vacation package to Chesterfield. With all your travel arrangements in order before you go, all you need to do here is focus on having the time of your life. Fill your free time with tours of Spofford Lake, Asbury United Methodist Church and Madame Sherris Castle Ruins, some of the top attractions you really should see during your trip to Chesterfield. Whoever you're taking a break with and whatever the size of your budget, your ultimate Chesterfield vacation is just a few clicks away with Expedia.

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
A Hotel Inn Sunapee

A Hotel Inn Sunapee

3 out of 5
Save 100% on your flight
Price was $576, price is now $403 per person
$403
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (739 reviews)
Very clean, comfortable bed. Great ambience!

Reviewed on Aug 13, 2025

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $1,382, price is now $1,032 per person
$1,032
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
7/10 Good! (1,002 reviews)
The daytime desk clerk is very rude!!

Reviewed on Aug 9, 2025

Moultonborough Inn

Moultonborough Inn

3 out of 5
Price was $683, price is now $511 per person
$511
per person
Oct 7 - Oct 11
just found
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9/10 Wonderful! (173 reviews)
Beds were great, everything is new. Kitchenette is convenient. Convenience store right next door. I messaged that stairs are a problem and they called and emailed that we would be on the first floor. Not much room in the bathroom, only sink is part of kitchenette, but there is counter space for toiletries there.

Reviewed on Aug 11, 2025

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $579, price is now $448 per person
$448
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
9/10 Wonderful! (138 reviews)
Well appointed and well maintained condos for any size party. Pemi Burger is outstanding and of course, you cannot beat the location.

Reviewed on Aug 17, 2025

The Centennial

The Centennial

4 out of 5
Price was $589, price is now $498 per person
$498
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
8.8/10 Excellent! (989 reviews)
Absolutely beautiful. Clean. Great staff. Classy! Definitely go back for sure.

Reviewed on Aug 22, 2025

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Discover the most popular places to visit in Chesterfield

Asbury United Methodist Church

You can learn about the history of Chesterfield with a trip to Asbury United Methodist Church. Amble around the area's riverfront, or seek out its ski slopes.

Asbury United Methodist Church

Chesterfield Hotel Deals

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
$125 nightly
The price is $136 total per night from Aug 31 to Sep 1
$136 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (882 reviews)
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash ..."

Reviewed on Aug 23, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $139 total per night from Aug 27 to Aug 28
$139 total
Aug 27 - Aug 28
Total with taxes and fees
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on Aug 22, 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
$121 nightly
The price is $133 total per night from Sep 2 to Sep 3
$133 total
Sep 2 - Sep 3
Total with taxes and fees
8/10 Very Good! (870 reviews)
"very friendly , clean and quiet, i would for sure stay if i come this way again. room is nice, beds comfy ,bathroom nice."

Reviewed on Aug 20, 2025

Hampton Inn Brattleboro
See all 495 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.

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $403 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'd like to snag a cheap Chesterfield vacation package, consider visiting in October, November and December. You'll typically find lower prices on flights and accommodations during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chesterfield?
With a well-planned schedule, you can easily hit the main Chesterfield sights in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Chesterfield vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield trip should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.