Chesterfield Vacation Packages

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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.

Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Merrimack by IHG

Holiday Inn Express & Suites Merrimack by IHG

2.5 out of 5
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Hotel is very dated.

Reviewed on Aug. 3, 2025

The Centennial

The Centennial

4 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
8.8/10 Excellent! (967 reviews)
The property was more attractive than most chain hotels. It was quite easy to find. The room was attractive and bed was comfortable. Breakfast was basic and not well stocked—one apple, one orange, and one carafe of coffee. The decaf had not been refilled. There were no plates or trays on which to put food and coffee, so it was hard to take coffee, fruit, toast etc. to the table. The bagels, jam, and yoghurt were good. That said, I would probably go there again when I need lodging in Concord.

Reviewed on Aug. 5, 2025

Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

2.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
8.4/10 Very Good! (1,000 reviews)
The only thing was that the shower had mildew very visibly growing in it at the bottom. Everything else was fine.

Reviewed on Aug. 4, 2025

Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
8.4/10 Very Good! (1,003 reviews)
The furniture was old and broken and the carpet was stained

Reviewed on Aug. 5, 2025

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

2.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Manchester (MHT)
9.4/10 Exceptional! (1,000 reviews)
The staff here was very friendly and the location convenient for access to BNH Pavillion show. Everything is clean and what one would expect of a Holiday Inn Express - a solid if unspectacular option...

Reviewed on Aug. 4, 2025

Ready to book your vacation to Chesterfield?

 

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Chesterfield Hotel Deals

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Aug 10 to Aug 11
CA $193
CA $212 total
Aug 10 - Aug 11
includes taxes & fees
6.6/10 (1,000 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on Jul. 28, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is CA $167 per night from Sep 4 to Sep 5
CA $167
CA $184 total
Sep 4 - Sep 5
includes taxes & fees
8/10 Very Good! (858 reviews)
"this is a very nice hotel, and we have stayed before and will stay again, but we will never stay in 212 again, they play music in the lobby and halls 24/7 which is fine, but 212 is right over the lobby and you can hear the drumming all night, it is very irritating, but like I said we have stayed ..."

Reviewed on Aug. 4, 2025

Hampton Inn Brattleboro
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
The price is CA $172 per night from Aug 12 to Aug 13
CA $172
CA $187 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very Good! (865 reviews)
"So happy we found this hotel. Our second stay in 3 weeks. Great location, very comfortable and clean. Staff is wonderful."

Reviewed on Aug. 2, 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 503 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'll find cheap prices from CA $813 on Expedia for your Chesterfield escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
You're likely to find reduced prices and better availability in January, February and March. Check out our cheap Chesterfield vacation packages and you could get some excellent off-season deals.
How many days is enough for Chesterfield?
With a well-organized itinerary, you can easily hit the most popular Chesterfield attractions in a handful of days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Finding a cheap Chesterfield package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your Chesterfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chesterfield?
If you have your Chesterfield vacation dates confirmed, book as early as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Chesterfield?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Chesterfield.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Chesterfield.
  3. Work out your trip length: Think about how much time you want to spend discovering Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Chesterfield vacation package.

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