Chesterfield Vacations from $687

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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.
Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
Price was $812, price is now $687 per person
$687
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
8.6/10 Excellent! (871 reviews)
Rooms were clean. Staff was helpful, but very disappointed with the noise from the air conditioner all night long along with the loud refrigerator running.

Reviewed on Aug 23, 2025

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $932, price is now $792 per person
$792
per person
Nov 23 - Nov 28
found 11 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
7/10 Good! (1,005 reviews)
It’s fine. Decently clean and quiet. The remote wouldn’t control the tv except to turn it off and on sometimes. Lots of little areas where the wear and tear is showing for an older hotel (peeling paint/stains etc).

Reviewed on Oct 3, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $1,309, price is now $1,125 per person
$1,125
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
9.6/10 Exceptional! (345 reviews)
Clean room. Luxurious and beautiful 😍

Reviewed on Oct 5, 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, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

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 Oct 26 to Oct 27
$136 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (914 reviews)
"💞"

Reviewed on Oct 5, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $75 total per night from Nov 9 to Nov 10
$75 total
Nov 9 - Nov 10
Total with taxes and fees
5.4/10 (571 reviews)
Fine room, right next to I-91 exit.
"Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables ..."

Reviewed on Sep 2, 2025

Econo Lodge Brattleboro
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $119 total per night from Oct 13 to Oct 14
$119 total
Oct 13 - Oct 14
Total with taxes and fees
7.6/10 Good! (1,005 reviews)
"We were initially put off by the look of the outside of this “Inn”! But it turns out we were greeted by a smiling and polite person during check in. The room was large, clean, and comfortable. The bathroom had thick towels and well stocked. All and all it was a very pleasant stay at a very reasonable ..."

Reviewed on Oct 4, 2025

The Covered Bridge Inn
See all 494 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.

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 $687 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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