Chesterfield Vacations from $257

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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.
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $345, price is now $257 per person
$257
per person
Dec 26 - Dec 28
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
18/10 Exceptional! (153 reviews)
Everything is excellent

Reviewed on Nov 23, 2025

The Centennial

The Centennial

4 out of 5
Price was $470, price is now $301 per person
$301
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Manchester (MHT)
17.6/10 Exceptional! (1,000 reviews)
The staff were great. The room was clean and nice. We had a window problem that was corrected quickly. Toiletries were fine. The only reason for a 4 rating is the continental breakfast was not good - the bagels, muffins & pastry were stale and the coffee was not good. It was a great location. Unfortunately many stores and restaurants were closed on Sundays & Mondays, not the hotel’s fault something to note if visiting Concord NH.

Reviewed on Nov 18, 2025

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Price was $441, price is now $330 per person
$330
per person
Dec 26 - Dec 28
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
18.8/10 Exceptional! (38 reviews)
Easy check-in, checkout; clean room; ready coffee machine! Quiet and cozy!

Reviewed on Nov 9, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $626, price is now $479 per person
$479
per person
Dec 26 - Dec 28
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
19.2/10 Exceptional! (352 reviews)
Loved our stay was very relaxing, had room with fireplace, it was wonderful! Love the dining options! Great for a quick weekend trip!

Reviewed on Nov 16, 2025

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
Price was $416, price is now $323 per person
$323
per person
Dec 26 - Dec 28
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
18.8/10 Exceptional! (432 reviews)
The room was very clean and the place was quiet

Reviewed on Nov 17, 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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $158 total per night from Nov 30 to Dec 1
$158 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (920 reviews)
Yes

Reviewed on Nov 16, 2025

Hampton Inn Brattleboro
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
$110 nightly
The price is $121 total per night from Dec 21 to Dec 22
$121 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (730 reviews)
Great convenient spot just off the highway. The room was clean and the amenities were just right.

Reviewed on Nov 8, 2025

Comfort Inn & Suites Brattleboro I-91
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
$139 nightly
The price is $151 total per night from Nov 25 to Nov 26
$151 total
Nov 25 - Nov 26
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
I received accommodations from Sarah of the hotel staff that were above and beyond my expectations. My colleague and I were travelling for work and we accidentally both booked rooms for the night. Sarah was able to cancel my colleague's reservation for with no hassle whatsoever. Thank you Sarah!

Reviewed on Nov 17, 2025

Best Western Plus Keene Hotel
See all 515 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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
3,800
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Colonial Theatre, Pisgah State Park and Cheshire Childrens Museum

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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 $257 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.

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