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 Durham by IHG
CA $950
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Manchester (MHT)
8.6/10 Excellent! (990 reviews)
The room was clean and breakfast good. The attendee for the breakfast area was helpful. Parking is ok. Overall a good place to stay.
Reviewed on Aug 18, 2026
Anchor at Tideline
CA $1,200
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Manchester (MHT)
10/10 Exceptional! (22 reviews)
The instructions for the code were incorrect so we couldn't get in the room. Fortunately there were two very helpful members of staff still there to help solve the problem and contact the owner. Glad we didn't arrive after 11 or we would have been out of luck.
Reviewed on Aug 18, 2026
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
CA $159
CA $172 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Nice stay and good location"
Reviewed on Aug 18, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
CA $207
CA $224 total
Aug 23 - Aug 24
includes taxes & fees
8.4/10 Very good! (1,006 reviews)
"Lori, the breakfast manager, was so helpful me check food ingredients for a food allergy. All the staff was pleasant, but Lori stands out."
Reviewed on Aug 18, 2026
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $104
CA $114 total
Aug 25 - Aug 26
includes taxes & fees
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.
Stay near popular Chesterfield attractions
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.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Make some time to visit the shops while you're in the area.
Frequently asked questions
How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $743 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?
- 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.
- 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.
- 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.
- 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.
