Chesterfield Vacations from $558

Book a Hotel + Flight or Car together to unlock savings

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.
InnSeason Resorts Pollard Brook

InnSeason Resorts Pollard Brook

3 out of 5
Price was $728, price is now $558 per person
$558
per person
Jun 25 - Jun 28
found 2 hours ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
9.4/10 Exceptional! (888 reviews)
Honestly best hotel I’ve ever been to

Reviewed on Apr 29, 2026

The Lake Estate on Winnisquam

The Lake Estate on Winnisquam

4.5 out of 5
Save 100% on your flight
Price was $2,715, price is now $1,802 per person
$1,802
per person
Aug 1 - Aug 8
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Manchester (MHT)
9.6/10 Exceptional! (15 reviews)
Exceptional place beautiful landscape and very relaxing

Reviewed on May 10, 2026

The Centennial

The Centennial

4 out of 5
Save 100% on your flight
Price was $1,158, price is now $824 per person
$824
per person
Aug 1 - Aug 8
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Lovely and very helpful staff - Late night and early morning! Bed was very comfortable and breakfast was out early and very nice.

Reviewed on Apr 6, 2026

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $1,142, price is now $876 per person
$876
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Manchester (MHT)
9.2/10 Wonderful! (209 reviews)
The property is good for skying in the area. Nothing fancy, but works perfectly for families who are out all day.

Reviewed on Apr 19, 2026

Cranmore Mountain Lodge Bed & Breakfast

Cranmore Mountain Lodge Bed & Breakfast

3 out of 5
Kearsarge
Price was $851, price is now $663 per person
$663
per person
Jun 25 - Jun 28
found 2 hours ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
8.8/10 Excellent! (249 reviews)
The breakfast was so delicious and they used fresh ingredients. The atmosphere made you feel like home. It was so cozy and relaxing.

Reviewed on May 10, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all trips

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
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (973 reviews)
Great experience

Reviewed on May 8, 2026

Hampton Inn Brattleboro
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
$154 nightly
The price is $167 total per night from May 13 to May 14
$167 total
May 13 - May 14
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
Not a pleasant experience! We had a water leak in our room, no hot water the second morning, and someone was in our room snd left a comforter on our bed! BUT, the front desk staff said they couldn’t see anything wrong…they couldn’t understand why we were so upset about it…someone had entered our ...

Reviewed on May 12, 2026

Best Western Plus Keene Hotel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $145 total per night from May 17 to May 18
$145 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (879 reviews)
Everything was as it is described. Restful night sleep.

Reviewed on May 12, 2026

Latchis Hotel
See all 526 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this top destination from $558 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

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