Chesterfield Vacations from $284

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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.
Hotel Coolidge

Hotel Coolidge

3 out of 5
Price was $350, price is now $284 per person
$284
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Houston (HOU) to Manchester (MHT)
8.2/10 Very Good! (1,000 reviews)
The hotel staff are all very very friendly. I like them a lot! The building is an old apartment building, not an excellent property, but pretty well managed. My suggestion to guest here is to not have breakfast in the downstair smoothie place. The smoothie is made out of some pre-mixed powder and did not strike us to be healthy or tasty. And it is expensive. I like the Turkish restaurant on the corner - forgot its name - though also pretty expensive. it seems nothing around the area is priced reasonably, the difference is quality.

Reviewed on Aug 18, 2025

The Centennial

The Centennial

4 out of 5
Save 100% on your flight
Price was $483, price is now $304 per person
$304
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Houston (HOU) to Manchester (MHT)
8.8/10 Excellent! (977 reviews)
The room and bathroom were spacious and clean although the air conditioning had a hard time keeping up in the oppressive heat. The breakfast didn’t have much of a selection.

Reviewed on Aug 18, 2025

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $371, price is now $284 per person
$284
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Houston (HOU) to Manchester (MHT)
7/10 Good! (1,004 reviews)
The daytime desk clerk is very rude!!

Reviewed on Aug 9, 2025

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $657, price is now $510 per person
$510
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Manchester (MHT)
9/10 Wonderful! (132 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 Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $1,501, price is now $1,195 per person
$1,195
per person
Oct 28 - Nov 2
found 23 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Manchester (MHT)
9.6/10 Exceptional! (342 reviews)
It was in a beautiful area.

Reviewed on May 30, 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 26 to Aug 27
$136 total
Aug 26 - Aug 27
Total includes taxes and fees
8.4/10 Very Good! (880 reviews)
"Nice stay. Good value"

Reviewed on Aug 18, 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 Sep 14 to Sep 15
$139 total
Sep 14 - Sep 15
Total includes taxes and fees
6.6/10 (1,006 reviews)
"Staff was helpful. Quiet area"

Reviewed on Aug 17, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
$122 nightly
The price is $135 total per night from Sep 2 to Sep 3
$135 total
Sep 2 - Sep 3
Total includes taxes and fees
8/10 Very Good! (866 reviews)
"Great beach and nice rooms Breakfast can improve and pool is small"

Reviewed on Aug 17, 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 $284 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.